Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives

ABSTRACT

The invention relates to new 1-H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) ##STR1## in which A and B together with the carbon atom to which they are bonded represent a substituted cycle, 
     X represents alkyl, halogen or alkoxy, 
     Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl, 
     Z represents alkyl, halogen or alkoxy, 
     n represents 0, 1, 2 or 3, 
     G is defined in the claims, 
     to processes for their preparation, and to their use as pesticides.

This is a division of application Ser. No. 08/140,635, filed on Oct. 21,1993, now U.S. Pat. No. 5,462,913.

The invention relates to 1-H-3-aryl-pyrrolidine-2,4-dione derivatives,to a plurality of processes for their preparation and to their use aspesticides (in particular as insecticides and acaricides) and asherbicides.

It has previously been described that 3-acyl-pyrrolidine-2,4-diones havepharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull 15 1120(1967)). N-Phenyl-pyrrolidine-2,4-diones were furthermore synthesized byR. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985 1095). Abiological activity of these compounds has not been described.

EP-A 0,262,399 discloses compounds which have a similar structure(3-aryl-pyrrolidine-2,4-diones), but nothing has been disclosed aboutthem as having a herbicidal, insecticidal or acaricidal activity.Unsubstitutedt bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A355 599) and (EP 415,211) as well as substituted monocyclic3-aryl-pyrrolidine-2,4-dione derivatives (EP-A377,893, EP 442,077, andEP 497 127)have been disclosed and have a herbicidal, insecticidal oracaricidal activity.

Polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP 442 073),substituted bicyclic 3-arylpyrrolidine-2,4-diones as well as1-H-3-arylpyrrolidine-dione derivatives (EP 456 063, EP 521 334, EP 501129) have also been disclosed.

New substituted spirocyclic 1-H-3-aryl-pyrolidine-2,4-dione derivativesof the formula (I) ##STR2## have now been found, in which

A and B together with the carbon atom to which they are bonded representa substituted cycle,

X represents alkyl, halogen or alkoxy,

Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl,

Z represents alkyl, halogen or alkoxy,

n represents 0, 1, 2 or 3,

G represents hydrogen (a) or the groups ##STR3## E represents a metalion equivalent or an ammonium ion, L and M represent oxygen and/orsulphur,

R¹ represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl,which can be interrupted by hetero atoms, optionally substituted phenyl,optionally substituted phenylalkyl, substituted hetaryl, substitutedphenoxyalkyl or substituted hetaryloxyalkyl,

R² represents in each case optionally halogen-substituted alkyl alkenyl,alkoxyalkyl, polyalkoxyalkyl or in each case optionally substitutedphenyl or benzyl,

R³, R⁴ and R⁵ independently of one another represent in each caseoptionally halogen-substituted alkyl, alkoxy, alkylamino, dialkyamino,alkylthio, alkenylthio, cycloalkylthio and in each case optionallysubstituted phenyl, phenoxy or phenylthio,

R⁶ and R⁷ independently of one another represent hydrogen, in each caseoptionally halogen-substituted alkyl, alkenyl, alkoxy, alkoxyalkyl, orrepresent optionally substituted phenyl, optionally substituted benzyl,or, together with the adjacent N-atom, represent a cycle which isoptionally interrupted by oxygen or sulphur.

Taking into account the various meanings (a), (b), (c), (d), (e), and(f) of group G of the general formula (I), the following main structures(Ia) to (Ig) result: ##STR4## in which A, B, E, L, M, X, Y, Z, R¹, R²,R³, R⁴, R⁵, R⁶, R⁷ and n have the abovementioned meanings.

Due to one or more chiral centres, the compounds of the formula(Ia)-(Ig) are generally obtained in the form of a stereoisomer mixturewhich can be resolved, if appropriate, in the customary manner. They canbe used in the form of their diasteromer mixtures as well as in the formof pure diasteromers or enantiomers. The text hereinafter will alwaysdiscuss compounds of the formula (Ia) to (Ig), for the sake ofsimplicity, even though this is to be understood as meaning the purecompounds as well as the mixtures which contain various proportions ofisomeric, enantiomeric and stereomeric compounds.

Furthermore, it has been found that the new substituted1-H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) areobtained by one of the processes described below.

(A) 1-H-3-Aryl-pyrrolidine-2,4-diones or their enols of the formula (Ia)##STR5## in which A, B, X, Y, Z and n have the abovementioned meaning,

are obtained when

N-acylamino acid esters of the formula (II) ##STR6## in which A, B, X,Y, Z and n have the abovementioned meaning and

R⁸ represents alkyl

are subjected to an intramolecular condensation reaction in the presenceof a diluent and in the presence of a base;

or

(B) compounds of the formula (Ib) ##STR7## in which A, B, X, Y, Z, R¹and n have the abovementioned meaning

are obtained when compounds of the formula (Ia) ##STR8## in which A, B,X, Y, Z and n have the abovementioned meaning

(α) are reacted with acid halides of the general formula (III) ##STR9##in which R¹ has the abovementioned meaning and

Hal represents halogen, in particular chlorine and bromine,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent,

or

(β) are reacted with carboxylic anhydrides of the general formula (IV)

    R.sup.1 --CO--O--CO--R.sup.1                               (IV)

in which

R¹ has the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent;

or

(C) compounds of the formula (Ic-1) ##STR10## in which A, B, X, Y, Z, R²and n have the abovementioned meaning

and

M represents oxygen or sulphur

are obtained when compounds of the formula (Ia) ##STR11## in which A, B,X, Y, Z and n have the abovementioned meaning, are reacted withchloroformic ester or chloroformic thioester of the general formula (V)

    R.sup.2 --M--CO--Cl                                        (V)

in which

R² and M have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent;

or

(D) compounds of the formula (Ic-2) ##STR12## in which A, B, R², X, Y, Zand n have the abovementioned meaning

and

M represents oxygen or sulphur

are obtained when compounds of the formula (Ia) ##STR13## in which A, B,X, Y, Z and n have the abovementioned meaning

α) are reacted with chloromonothioformic esters or chlorodithioformicesters of the general formula (VI) ##STR14## in which M and R² have theabovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of a acid-binding agent,

or

β) are reacted with carbon disulphide and subsequently with alkylhalides of the general formula (VII)

    r.sup.2 --Hal                                              (VII)

in which

R² has the abovementioned meaning

and

Hal represents chlorine, bromine or iodine; optionally in the presenceof a diluent or an acid binding agent or

(E) compounds of the formula (Id) ##STR15## in which A, B, X, Y, Z, R³and n have the abovementioned meaning

are obtained when compounds of the formula (Ia) ##STR16## in which A, B,X, Y, Z and n have the abovementioned meaning

are reacted with sulphonyl chlorides of the general formula (VII)

    R.sup.3 --SO.sub.2 --Cl                                    (VIII)

in which

R³ has the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent;

or

(F) compounds of the formula (Ie) ##STR17## in which A, B, L, X, Y, Z,R⁴, R⁵ and n have the abovementioned meaning

are obtained when

1-H-3-aryl-pyrrolidine-2,4-diones of the formula (Ia) or their enoles##STR18## in which A, B, X, Y, Z and n have the abovementioned meaning

are reacted with phosphorus compounds of the general formula (IX)##STR19## in which L, R⁴ and R⁵ have the abovementioned meaning

and

Hal represents halogen, in particular chlorine and bromine;

optionally in the presence of a diluent or an acid binding agent or

(G) compounds of the formula (If) ##STR20## in which A, B, X, Y, Z and nhave the abovementioned meaning

and

E represents a metal ion equivalent or an ammonium ion

are obtained when compounds of the formula (Ia) ##STR21## in which A, B,X, Y, Z and n have the abovementioned meaning

are reacted with metal hydroxides or amines of the general formula (X)and (XI) ##STR22## in which Me represents mono- or divalent metal ions,

s and t represent the number 1 and 2 and

R⁵, R⁶ and R⁷ independently of one another represent hydrogen and alkyl,

if appropriate in the presence of a diluent.

(H) Furthermore, it has been found that compounds of the formula (g)##STR23## in which A, B, L, X, Y, Z, R⁶, R⁷ and n have theabove-mentioned meaning

are obtained when compounds of the formula (Ia) ##STR24## in which A, B,X, Y, Z and n have the abovementioned meaning,

α) are reacted with compounds of the general formula (XII)

    R.sup.6 --N═C═L                                    (XII)

in which

L and R⁶ have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst,

or

β) are reacted with carbamoyl chlorides or thiocarbamoyl chlorides ofthe general formula (XIII) ##STR25## in which L, R⁶ and R⁷ have theabovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent.

Furthermore, it has been found that the new1-H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) aredistinguished by outstanding insecticidal, acaricidal and herbicidalactivities.

The following applies to the general formulae of the presentapplication:

A, B and the carbon atom to which they are bonded preferably represent aC₃ -C₆ -spirocycle which can be monosubstituted or polysubstituted byalkyl, cycloalkyl, haloalkyl, alkoxy, thioalky, halogen or phenyl, or

A, B and the carbon atom to which they are bonded preferably represent aC₃ -C₆ -spirocycle which is substituted by an alkylenediyl group whichis optionally interrupted by one or two oxygen and/or sulphur atoms orby an alkylenedioxyl or an alkylenedithioyl group, which group, togetherwith the carbon atom to which it is bonded, forms a further five- toeight-membered spirocycle, or

A,B and the carbon atom to which they are bonded preferably represent aC₃ -C₆ -spirocycle in which two substituents together with the C-atomsto which they are bonded represent a saturated or unsaturated carbocyclewhich is optionally substituted by alkyl, alkoxy or halogen and which isoptionally interrupted by oxygen or sulphur atom.

A, B and the carbon atom to which they are bonded particularlypreferably represent a C₃ -C₆ -spirocycle which can be monosubstitutedor polysubstituted by C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₃-haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -thioalkyl, fluorine, chlorine orphenyl, or

A, B and the carbon atom to which they are bonded particularlypreferably represent a C₃ -C₆ -spirocycle which is substituted by analkylenediyl group which is optionally interrupted by one or two oxygenor sulphur atoms or by an alkylenedioxyl or an alkylenedithiooxyl groupwhich, together with the carbon atom to which it is bonded, forms afurther five- to seven-membered spirocycle, or

A, B and the carbon atom to which they are bonded particularlypreferably represent a C₃ -C₆ -spirocycle in which two substituentstogether with the C-atoms to which they are bonded represent a saturatedor unsaturated carbocyle which is substituted by alkyl(C₁ -C₃),alkoxy(C₁ -C₃), or fluorine, chlorine or bromine and which is optionallyinterrupted by oxygen or sulphur atom.

A, B and the carbon atom to which they are bonded very particularlypreferably represent a C₃ -C₆ -spirocycle which can be at leastmonosubstituted or polysubstituted by methyl, ethyl, propyl, isopropyl,butyl, iso-butyl, sec.-butyl, tert,-butyl, cyclo-hexyl, trifluoromethyl,methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy,tert-butoxy, methylthio, fluorine, chlorine or phenyl or

A, B and the carbon atom to which they are bonded very particularlypreferably represent a C₃ -C₆ -spirocycle which is substituted by analkylenediyl group which is optionally interrupted by an oxygen orsulphur atom or by an alkylenedioxyl group, which group, together withthe carbon atom to which it is bonded, forms a further five- toseven-membered spirocycle,

A, B and the carbon atom to which they are bonded very particularlypreferably represent a C₃ -C₆ -spirocycle in which two substituentstogether with the carbon atoms to which they are bonded represent asaturated or unsaturated five- or six-membered cycle, which isoptionally interrupted by oxygen or sulphur.

X preferably represents C₁ -C₆ -alkyl, halogen or C₁ -C₆ -alkoxy.

X particularly preferably represents C₁ -C₄ -alkyl, halogen or C₁ -C₄-alkoxy.

X very particularly preferably represents methyl, ethyl, propyl,2-propyl, fluorine, chlorine, bromine, methoxy or ethoxy.

Y preferably represents hydrogen, C₁ -C₆ -alkyl, halogen, C₁ -C₆ -alkoxyor C₁ -C₃ -halogenoalkyl.

Y particularly preferably represents hydrogen, C₁ -C₄ -alkyl, halogen,C₁ -C₄ -alkoxy or C₁ -C₂ -halogenoalkyl.

Y very particularly preferably represents hydrogen, methyl, ethyl,propyl, i-propyl, butyl, i-butyl, tert.-butyl, fluorine, chlorine,bromine, methoxy, ethoxy or trifluoromethyl.

Z preferably represents C₁ -C₆ -alkyl, halogen or C₁ -C₆ -alkoxy.

Z particularly preferably represents C₁ -C₄ -alkyl, halogen or C₁ -C₄-alkoxy.

Z very particularly preferably represents methyl, ethyl, propyl,i-propyl, butyl, i-butyl, tert.-butyl, fluorine, chlorine, bromine,methoxy or ethoxy.

n preferably means whole figures from 0 to 3.

n particularly preferably means 0, 1 or 2.

n very particularly preferably means 0 or 1.

G preferably represents hydrogen (a) or the groups ##STR26## in which Ea metal ion equivalent or an ammonium ion and

L and M in each case represent oxygen and/or sulphur,

represents in each case optionally halogen-substituted C₁ -C₂₀ -alkyl,C₂ -C₂₀ -alkenyl, C₁ -C₈ -alkoxy-C₂ -C₈ -alkyl, C₁ -C₈ -alkylthio-C₂ -C₈-alkyl, C₁ -C₈ -polyalkoxy-C₂ -C₈ -alkyl or cycloalkyl which has 3 to 8ring atoms and which can be interrupted by oxygen and/or sulphur atoms,

or represents phenyl which is optionally substituted by halogen, nitro,C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl or C₁ -C₆-halogenoalkoxy,

or represents phenyl-C₁ -C₆ -alkyl which is optionally substituted byhalogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl or C₁ -C₆-halogenoalkoxy,

or represents hetaryl which is optionally substituted by halogen and/orC₁ -C₆ -alkyl,

or represents phenoxy-C₁ -C₆ -alkyl which is optionally substituted byhalogen and C₁ -C₆ -alkyl,

or represents hetaryloxy-C₁ -C₆ -alkyl which is optionally substitutedby halogen, amino and C₁ -C₆ -alkyl,

R² represents in each case optionally halogen-substituted C₁ -C₂₀-alkyl, C₃ -C₂₀ -alkenyl, C₁ -C₈ -alkoxy-C₂ -C₈ -alkyl, C₁ -C₈-polyalkoxy-C₂ -C₈ -alkyl, or represents phenyl or benzyl, in each caseoptionally substituted by halogen, nitro, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxyor C₁ -C₆ -halogenoalkyl,

R³, R⁴ and R⁵ independently of one another represent in each caseoptionally halogen-substituted C₁ -C₈ -alkyl, C₁ -C₈ -alkoxy, C₁ -C₈-alkylamino, di-(C₁ -C₈)-alkylamino, C₁ -C₈ -alkylthio, C₂ -C₃-alkenylthio, C₃ -C₇ -cycloalkylthio, or represent phenyl, phenoxy orphenylthio, in each case optionally substituted by halogen, nitro,cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-halgenoalkylthio, C₁ -C₄ -alkyl or C₁ -C₄ -halogenoalkyl,

R⁶ and R⁷ independently of one another represent hydrogen, or representin each case optionally halogen-substituted CV₁ -C₈ -alkyl, C₃ -C₈-cycloalkyl, C₁ -C₈ -alkoxy, C₃ -C₈ -alkenyl or C₁ -C₈ -alkoxy-C₂ -C₈-alkyl, or represent phenyl which is optionally substituted by halogen,C₁ -C₈ -halogenoalkyl, C₁ -C₈ -alkyl or C₁ -C₈ -alkoxy, or representbenzyl which is optionally substituted by halogen, C₁ -C₈ -alkyl, C₁ -C₈-halogenoalkyl or C₁ -C₈ -alkoxy, or together represent a C₃ -C₆-alkylene ring which is optionally interrupted by oxygen or sulphur,

G particularly preferably represents hydrogen (a) or the groups##STR27## in which E represents a metal ion equivalent or an ammoniumion,

L and M in each case represent oxygen and/or sulphur,

R¹ represents in each case optionally halogen-substituted C₁ -C₁₆-alkyl, C₂ -C₁₆ -alkenyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₁ -C₁₆-alkylthio-C₂ -C₆ -alkyl, C₁ -C₆ -polyalkoxy-C₂ -C₆ -alkyl or cycloalkylwhich has 3 to 7 ring atoms and which can be interrupted by 1-2 oxygenand/or sulphur atoms,

or represents phenyl which is optionally substituted by halogen, nitro,C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkyl or C₁ -C₃-halogenoalkoxy,

or represents phenyl-C₁ -C₄ -alkyl which is optionally substituted byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkyl or C₁ -C₃-halogenoalkoxy,

or represents hetaryl which is optionally substituted by fluorine,chlorine, bromine and/or C₁ -C₄ -alkyl,

or represents phenoxy-C₁ -C₅ -alkyl which is optionally substituted byfluorine, chlorine, bromine and C₁ -C₄ -alkyl,

or represents hetaryloxy-C₁ -C₅ -alkyl which is optionally substitutedby fluorine, chlorine, bromine, amino and C₁ -C₄ -alkyl,

R² represents in each case optionally halogen-substituted C₁ -C₁₆-alkyl, C₃ -C₁₆ -alkenyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₁ -C₆-polyalkoxy-C₂ -C₆ -alkyl or,

or represents phenyl or benzyl, in each case optionally substituted byhalogen, nitro, C₁ -C₄ -alkyl, C₁ -C₃ -alkoxy or C₁ -C₃ -halogenoalkyl,

R³, R⁴ and R⁵ independently of one another represent in each caseoptionally halogen-substituted C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆-alkylamino, di-,(C₁ -C₆)-alkylamino, C₁ -C₆ -alkylthio, C₃ -C₄-alkenylthio, C₃ -C₆ -cycloalkylthio, or represent phenyl, phenoxy orphenylthio, in each case optionally substituted by fluorine, chlorine,bromine, nitro, cyano, C₁ -C₃ -alkoxy, C₁ -C₃ -halogenoalkoxy, C₁ -C₃-alkylthio, C₁ -C₃ -halogenoalkylthio, C₁ -C₃ -alkyl or C₁ -C₃-halogenoalkyl,

R⁶ and R⁷ independently of one another represent hydrogen, or representoptionally halogen-substituted C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkoxy, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, or representphenyl which is optionally substituted by halogen, C₁ -C₅-halogenoalkyl, C₁ -C₅ -alkyl or C₁ -C₅ -alkoxy, or represent benzylwhich is optionally substituted by halogen, C₁ -C₅ -alkyl, C₁ -C₅-halogenoalkyl or C₁ -C₅ -alkoxy, or together represent a C₃ -C₆-alkylene ring which is optionally substituted by oxygen or sulphur,

G very particularly preferably represents hydrogen (a) or the groups##STR28## in which E represents a metal ion equivalent or an ammoniumion and

L and M represent oxygen and/or sulphur,

R¹ represents in each case optionally fluorine- or chlorine-substitutedC₁ -C₁₄ -alkyl, C₃ -C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkyl, C₁ -C₄-alkylthio-C₂ -C₆ -alkyl, C₁ -C₄ -polyalkoxy-C₂ -C₄ -alkyl or cycloalkylwhich has 3 to 6 ring atoms and which can be interrupted by 1 to 2oxygen and/or sulphur atoms,

or represents phenyl which is optionally substituted by fluorine,chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy,trifluoromethyl, trifluoromethoxy or nitro,

or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted byfluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy,ethoxy, trifluoromethyl or trifluoromethoxy,

or represents furanoyl, pyridyl, pyrimidyl, thiazolyl and pyrazolyl, ineach case optionally substituted by fluorine, chlorine, bromine, methylor ethyl,

or represents phenoxy-C₁ -C₄ -alkyl which is optionally substituted byfluorine, chlorine, methyl or ethyl,

or represents pyridyloxy-C₁ -C₄ -alkyl, pyrimidyloxy-C₁ -C₄ -alkyl andthiazolyloxy-C₁ -C₄ -alkyl, in each case optionally substituted byfluorine, chlorine, amino, methyl or ethyl,

R² represents in each case optionally fluorine- or chlorine substitutedC₁ -C₁₄ -alkyl, C₃ -C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkyl or C₁ -C₄-polyalkoxy-C₂ -C₆ -alkyl,

or represents phenyl or benzyl, in each case optionally substituted byfluorine, chlorine, nitro, methyl, ethyl, propyl, i-propyl, methoxy,ethoxy or trifluoromethyl,

R³, R⁴ and R⁵ independently of one another represent C₁ -C₄ -alkyl, C₁-C₄ -alkoxy, C₁ -C₄ -alkylamino, di-(C₁ -C₄)-alkylamino or C₁ -C₄-alkylthio, in each case optionally substituted by fluorine or chlorine,or represent phenyl, phenoxy or phenylthio, in each case optionallysubstituted by fluorine, chlorine, bromine, nitro, cyano, C₁ -C₂-alkoxy, C₁ -C₄ -fluoroalkoxy, C₁ -C₂ -alkylthio, C₁ -C₂-fluoroalkylthio or C₁ -C₃ -alkyl,

R⁶ and R⁷ independently of one another represent hydrogen, or representC₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxy, C₃ -C₄ -alkenyl or C₁-C₄ -alkoxy-C₂ -C₄ -alkyl, in each case optionally substituted byfluorine, chlorine or bromine, or represent phenyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ -halogenoalkyl, C₁-C₄ -alkyl or C₁ -C₄ -alkoxy, or represent benzyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄-halogenoalkyl or C₁ -C₄ -alkoxy, or together represent a C₄ -C₆-alkylene ring which is optionally substituted by oxygen or sulphur.

The following compounds of the formula (Ia) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples: ##STR29##

                  TABLE 1                                                         ______________________________________                                        X       Y        Z.sub.n  R.sub.a                                                                              R.sub.b                                                                             R.sub.c                                ______________________________________                                        Cl      Cl       H        H      CH.sub.3                                                                            H                                      Cl      Cl       H        H      H     CH.sub.3                               Cl      Cl       H        H      H     C.sub.2 H.sub.5                        Cl      Cl       H        H      H     i-C.sub.3 H.sub.7                      Cl      Cl       H        H      H     t-C.sub.4 H.sub.9                      Cl      Cl       H        H      CH.sub.3                                                                            CH.sub.3                               Cl      H        6-F      CH.sub.3                                                                             H     H                                      Cl      H        6-F      H      CH.sub.3                                                                            H                                      Cl      H        6-F      H      H     CH.sub.3                               Cl      H        6-F      H      H     C.sub.2 H.sub.5                        Cl      H        6-F      H      H     i-C.sub.3 H.sub.7                      Cl      H        6-F      H      H     t-C.sub.4 H.sub.9                      Cl      H        6-F      H      CH.sub.3                                                                            CH.sub.3                               Cl      H        6-Cl     CH.sub.3                                                                             H     H                                      Cl      H        6-Cl     H      CH.sub.3                                                                            H                                      Cl      H        6-Cl     H      H     CH.sub.3                               Cl      H        6-Cl     H      H     C.sub.2 H.sub.5                        Cl      H        6-Cl     H      H     i-C.sub.3 H.sub.7                      Cl      H        6-Cl     H      H     t-C.sub.4 H.sub.9                      Cl      H        6-Cl     H      CH.sub.3                                                                            CH.sub.3                               CH.sub.3                                                                              CH.sub.3 H        CH.sub.3                                                                             H     H                                      CH.sub.3                                                                              CH.sub.3 H        H      CH.sub.3                                                                            H                                      CH.sub.3                                                                              CH.sub.3 H        H      H     CH.sub.3                               CH.sub.3                                                                              CH.sub.3 H        H      H     C.sub.2 H.sub.5                        CH.sub.3                                                                              CH.sub.3 H        H      H     i-C.sub.3 H.sub.7                      CH.sub.3                                                                              CH.sub.3 H        H      H     i-C.sub.4 H.sub.9                      CH.sub.3                                                                              CH.sub.3 H        H      CH.sub.3                                                                            CH.sub.3                               CH.sub.3                                                                              CH.sub.3 6-CH.sub.3                                                                             H      CH.sub.3                                                                            H                                      CH.sub.3                                                                              CH.sub.3 6-CH.sub.3                                                                             H      H     C.sub.2 H.sub.5                        CH.sub.3                                                                              CH.sub.3 6-CH.sub.3                                                                             H      H     i-C.sub.3 H.sub.7                      CH.sub.3                                                                              CH.sub.3 6-CH.sub.3                                                                             H      H     t-C.sub.4 H.sub.9                      CH.sub.3                                                                              CH.sub.3 6-CH.sub.3                                                                             H      CH.sub.3                                                                            CH.sub.3                               ______________________________________                                    

The following compounds of the formula (Ib) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples: ##STR30##

                  TABLE 2                                                         ______________________________________                                        X    Y       Z.sub.n R.sub.a                                                                            R.sub.b                                                                             R.sub.c                                                                             R.sup.1                                 ______________________________________                                        Cl   Cl      H       CH.sub.3                                                                           H     H     CH.sub.3                                Cl   Cl      H       H    CH.sub.3                                                                            H     CH.sub.3                                Cl   Cl      H       H    H     CH.sub.3                                                                            CH.sub.3                                Cl   Cl      H       H    H     C.sub.2 H.sub.5                                                                     CH.sub.3                                Cl   Cl      H       H    H     i-C.sub.3 H.sub.7                                                                   CH.sub.3                                Cl   Cl      H       H    H     t-C.sub.4 H.sub.9                                                                   CH.sub.3                                Cl   Cl      H       H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                Cl   H       6-F     CH.sub.3                                                                           H     H     CH.sub.3                                Cl   H       6-F     H    CH.sub.3                                                                            H     CH.sub.3                                Cl   H       6-F     H    H     CH.sub.3                                                                            CH.sub.3                                Cl   H       6-F     H    H     C.sub.2 H.sub.5                                                                     CH.sub.3                                Cl   H       6-F     H    H     i-C.sub.3 H.sub.7                                                                   CH.sub.3                                Cl   H       6-F     H    H     t-C.sub.4 H.sub.9                                                                   CH.sub.3                                Cl   H       6-F     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                Cl   H       6-Cl    CH.sub.3                                                                           H     H     CH.sub.3                                Cl   H       6-Cl    H    CH.sub.3                                                                            H     CH.sub.3                                Cl   H       6-Cl    H    H     CH.sub.3                                                                            CH.sub.3                                Cl   H       6-Cl    H    H     C.sub.2 H.sub.5                                                                     CH.sub.3                                Cl   H       6-Cl    H    H     i-C.sub.3 H.sub.7                                                                   CH.sub.3                                Cl   H       6-Cl    H    H     t-C.sub.4 H.sub.9                                                                   CH.sub.3                                Cl   H       6-Cl    H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              H       CH.sub.3                                                                           H     H     CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            H     CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     CH.sub.3                                                                            CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     C.sub.2 H.sub.5                                                                     CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     i-C.sub.3 H.sub.7                                                                   CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     t-C.sub.4 H.sub.9                                                                   CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    CH.sub.3                                                                            H     CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H     CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     C.sub.2 H.sub.5                                                                     CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     i-C.sub.3 H.sub.7                                                                   CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     t-C.sub.4 H.sub.9                                                                   CH.sub.3                                CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                Cl   Cl      H       CH.sub.3                                                                           H     H     i-C.sub.3 H.sub.7                       Cl   Cl      H       H    CH.sub.3                                                                            H     i-C.sub.3 H.sub.7                       Cl   Cl      H       H    H     CH.sub.3                                                                            i-C.sub.3 H.sub.7                       Cl   Cl      H       H    H     C.sub.2 H.sub.5                                                                     i-C.sub.3 H.sub.7                       Cl   Cl      H       H    H     i-C.sub.3 H.sub.7                                                                   i-C.sub.3 H.sub.7                       Cl   Cl      H       H    H     t-C.sub.4 H.sub.9                                                                   i-C.sub.3 H.sub.7                       Cl   Cl      H       H    CH.sub.3                                                                            CH.sub.3                                                                            i-C.sub.3 H.sub.7                       Cl   H       6-F     CH.sub.3                                                                           H     H     i-C.sub.3 H.sub.7                       Cl   H       6-F     H    CH.sub.3                                                                            H     i-C.sub.3 H.sub.7                       Cl   H       6-F     H    H     CH.sub.3                                                                            i-C.sub.3 H.sub.7                       Cl   H       6-F     H    H     C.sub.2 H.sub.5                                                                     i-C.sub.3 H.sub.7                       Cl   H       6-F     H    H     i-C.sub.3 H.sub.7                                                                   i-C.sub.3 H.sub.7                       Cl   H       6-F     H    H     t-C.sub.4 H.sub.9                                                                   i-C.sub.3 H.sub.7                       Cl   H       6-F     H    CH.sub.3                                                                            CH.sub.3                                                                            i-C.sub.3 H.sub.7                       Cl   H       6-Cl    CH.sub.3                                                                           H     H     i-C.sub.3 H.sub.7                       Cl   H       6-Cl    H    CH.sub.3                                                                            H     i-C.sub.3 H.sub.7                       Cl   H       6-Cl    H    H     CH.sub.3                                                                            i-C.sub.3 H.sub.7                       Cl   H       6-Cl    H    H     C.sub.2 H.sub.5                                                                     i-C.sub.3 H.sub.7                       Cl   H       6-Cl    H    H     i-C.sub.3 H.sub.7                                                                   i-C.sub.3 H.sub.7                       Cl   H       6-Cl    H    H     t-C.sub.4 H.sub.9                                                                   i-C.sub.3 H.sub.7                       Cl   H       6-Cl    H    CH.sub.3                                                                            CH.sub.3                                                                            i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              H       CH.sub.3                                                                           H     H     i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            H     i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     CH.sub.3                                                                            i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     C.sub.2 H.sub.5                                                                     i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     i-C.sub.3 H.sub.7                                                                   i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     t-C.sub.4 H.sub.9                                                                   i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            CH.sub.3                                                                            i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            CH.sub.3                                                                           H     H     i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    CH.sub.3                                                                            H     i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     CH.sub.3                                                                            i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     C.sub.2 H.sub.5                                                                     i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     i-C.sub.3 H.sub.7                                                                   i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     t-C.sub.4 H.sub.9                                                                   i-C.sub.3 H.sub.7                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     CH.sub.3                                                                            i-C.sub.3 H.sub.7                       Cl   Cl      H       CH.sub.3                                                                           H     H     t-C.sub.4 H.sub.9                       Cl   Cl      H       H    CH.sub.3                                                                            H     t-C.sub.4 H.sub.9                       Cl   Cl      H       H    H     CH.sub.3                                                                            t-C.sub.4 H.sub.9                       Cl   Cl      H       H    H     C.sub.2 H.sub.5                                                                     t-C.sub.4 H.sub.9                       Cl   Cl      H       H    H     i-C.sub.3 H.sub.7                                                                   t-C.sub.4 H.sub.9                       Cl   Cl      H       H    H     t-C.sub.4 H.sub.9                                                                   t-C.sub.4 H.sub.9                       Cl   Cl      H       H    CH.sub.3                                                                            CH.sub.3                                                                            t-C.sub.4 H.sub.9                       Cl   H       6-F     CH.sub.3                                                                           H     H     t-C.sub.4 H.sub.9                       Cl   H       6-F     H    CH.sub.3                                                                            H     t-C.sub.4 H.sub.9                       Cl   H       6-F     H    H     CH.sub.3                                                                            t-C.sub.4 H.sub.9                       Cl   H       6-F     H    H     C.sub.2 H.sub.5                                                                     t-C.sub.4 H.sub.9                       Cl   H       6-F     H    H     i-C.sub.3 H.sub.7                                                                   t-C.sub.4 H.sub.9                       Cl   H       6-F     H    H     t-C.sub.4 H.sub.9                                                                   t-C.sub.4 H.sub.9                       Cl   H       6-F     H    CH.sub.3                                                                            CH.sub.3                                                                            t-C.sub.4 H.sub.9                       Cl   H       6-Cl    CH.sub.3                                                                           H     H     t-C.sub.4 H.sub.9                       Cl   H       6-Cl    H    CH.sub.3                                                                            H     t-C.sub.4 H.sub.9                       Cl   H       6-Cl    H    H     CH.sub.3                                                                            t-C.sub.4 H.sub.9                       Cl   H       6-Cl    H    H     C.sub.2 H.sub.5                                                                     t-C.sub.4 H.sub.9                       Cl   H       6-Cl    H    H     i-C.sub.3 H.sub.7                                                                   t-C.sub.4 H.sub.9                       Cl   H       6-Cl    H    H     t-C.sub.4 H.sub.9                                                                   t-C.sub.4 H.sub.9                       Cl   H       6-Cl    H    CH.sub.3                                                                            CH.sub.3                                                                            t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              H       CH.sub.3                                                                           H     H     t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            H     t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     CH.sub.3                                                                            t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     C.sub.2 H.sub.5                                                                     t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     i-C.sub.3 H.sub.7                                                                   t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     t-C.sub.4 H.sub.9                                                                   t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            CH.sub.3                                                                            t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            CH.sub.3                                                                           H     H     t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    CH.sub.3                                                                            H     t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     CH.sub.3                                                                            t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     C.sub.2 H.sub.5                                                                     t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     i-C.sub.3 H.sub.7                                                                   t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     t-C.sub.4 H.sub.9                                                                   t-C.sub.4 H.sub.9                       CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                            t-C.sub.4 H.sub.9                       Cl   Cl      H       CH.sub.3                                                                           H     H                                             Cl   Cl      H       H    CH.sub.3                                                                            H                                                                                    ##STR31##                              Cl   Cl      H       H    H     CH.sub.3                                                                             ##STR32##                              Cl   Cl      H       H    H     C.sub.2 H.sub.5                                                                      ##STR33##                              Cl   Cl      H       H    H     i-C.sub.3 H.sub.7                                                                    ##STR34##                              Cl   Cl      H       H    H     t-C.sub.4 H.sub.9                                                                    ##STR35##                              Cl   Cl      H       H    CH.sub.3                                                                            CH.sub.3                                                                             ##STR36##                              Cl   H       6-F     CH.sub.3                                                                           H     H                                                                                    ##STR37##                              Cl   H       6-F     H    CH.sub.3                                                                            H                                                                                    ##STR38##                              Cl   H       6-F     H    H     CH.sub.3                                                                             ##STR39##                              Cl   H       6-F     H    H     C.sub.2 H.sub.5                                                                      ##STR40##                              Cl   H       6-F     H    H     i-C.sub.3 H.sub.7                                                                    ##STR41##                              Cl   H       6-F     H    H     t-C.sub.4 H.sub.9                                                                    ##STR42##                              Cl   H       6-F     H    CH.sub.3                                                                            CH.sub.3                                                                             ##STR43##                              Cl   H       6-Cl    CH.sub.3                                                                           H     H                                                                                    ##STR44##                              Cl   H       6-Cl    H    CH.sub.3                                                                            H                                                                                    ##STR45##                              Cl   H       6-Cl    H    H     CH.sub.3                                                                             ##STR46##                              Cl   H       6-Cl    H    H     C.sub.2 H.sub.5                                                                      ##STR47##                              Cl   H       6-Cl    H    H     i-C.sub.3 H.sub.7                                                                    ##STR48##                              Cl   H       6-Cl    H    H     t-C.sub.4 H.sub.9                                                                    ##STR49##                              Cl   H       6-Cl    H    CH.sub.3                                                                            CH.sub.3                                                                             ##STR50##                              CH.sub.3                                                                           CH.sub.3                                                                              H       CH.sub.3                                                                           H     H                                                                                    ##STR51##                              CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            H                                                                                    ##STR52##                              CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     CH.sub.3                                                                             ##STR53##                              CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     C.sub.2 H.sub.5                                                                      ##STR54##                              CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     i-C.sub.3 H.sub.7                                                                    ##STR55##                              CH.sub.3                                                                           CH.sub.3                                                                              H       H    H     t-C.sub.4 H.sub.9                                                                    ##STR56##                              CH.sub.3                                                                           CH.sub.3                                                                              H       H    CH.sub.3                                                                            CH.sub.3                                                                             ##STR57##                              CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            CH.sub.3                                                                           H     H                                                                                    ##STR58##                              CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    CH.sub.3                                                                            H                                                                                    ##STR59##                              CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     CH.sub.3                                                                             ##STR60##                              CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     C.sub.2 H.sub.5                                                                      ##STR61##                              CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     i-C.sub.3 H.sub.7                                                                    ##STR62##                              CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     t-C.sub.4 H.sub.9                                                                    ##STR63##                              CH.sub.3                                                                           CH.sub.3                                                                              6-CH.sub.3                                                                            H    H     CH.sub.3                                                                             ##STR64##                              ______________________________________                                    

The following compounds of the formula (Ic) may be mentionedindividually in addition to the compounds mentioned in the preparationexamples: ##STR65##

                                      TABLE 3                                     __________________________________________________________________________    X  Y  Z.sub.n                                                                           R.sub.a                                                                           R.sub.b                                                                           R.sub.c                                                                            L  M  R.sup.2                                          __________________________________________________________________________    Cl Cl H   CH.sub.3                                                                          H   H    O  O  C.sub.2 H.sub.5                                  Cl Cl H   H   CH.sub.3                                                                          H    O  O  C.sub.2 H.sub.5                                  Cl Cl H   H   H   CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  Cl Cl H   H   H   C.sub.2 H.sub.5                                                                    O  O  C.sub.2 H.sub.5                                  Cl Cl H   H   H   i-C.sub.3 H.sub.7                                                                  O  O  C.sub.2 H.sub.5                                  Cl Cl H   H   H   t-C.sub.4 H.sub.9                                                                  O  O  C.sub.2 H.sub.5                                  Cl Cl H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  Cl H  6-F CH.sub.3                                                                          H   H    O  O  C.sub.2 H.sub.5                                  Cl H  6-F H   CH.sub.3                                                                          H    O  O  C.sub.2 H.sub.5                                  Cl H  6-F H   H   CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  Cl H  6-F H   H   C.sub.2 H.sub.5                                                                    O  O  C.sub.2 H.sub.5                                  Cl H  6-F H   H   i-C.sub.3 F.sub.7                                                                  O  O  C.sub.2 H.sub.5                                  Cl H  6-F H   H   t-C.sub.4 H.sub.9                                                                  O  O  C.sub.2 H.sub.5                                  Cl H  6-F H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  Cl H  6-Cl                                                                              CH.sub.3                                                                          H   H    O  O  C.sub.2 H.sub.5                                  Cl H  6-Cl                                                                              H   CH.sub.3                                                                          H    O  O  C.sub.2 H.sub.5                                  Cl H  6-Cl                                                                              H   H   CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  Cl H  6-Cl                                                                              H   H   C.sub.2 H.sub.5                                                                    O  O  C.sub.2 H.sub.5                                  Cl H  6-Cl                                                                              H   H   i-C.sub.3 H.sub.7                                                                  O  O  C.sub.2 H.sub.5                                  Cl H  6-Cl                                                                              H   H   t-C.sub.4 H.sub.9                                                                  O  O  C.sub.2 H.sub.5                                  Cl H  6-Cl                                                                              H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                          H   H    O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          H    O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   C.sub.2 H.sub.5                                                                    O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   i-C.sub.3 H.sub.7                                                                  O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   t-C.sub.4 H.sub.9                                                                  O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                          H   H    O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   CH.sub.3                                                                          H    O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   C.sub.2 H.sub.5                                                                    O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   i-C.sub.3 H.sub.7                                                                  O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   t-C.sub.4 H.sub.9                                                                  O  O  C.sub.2 H.sub.5                                  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O  C.sub.2 H.sub.5                                  Cl Cl H   CH.sub.3                                                                          H   H    O  O  i-C.sub.3 H.sub.7                                Cl Cl H   H   CH.sub.3                                                                          H    O  O  i-C.sub.3 H.sub.7                                Cl Cl H   H   H   CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                Cl Cl H   H   H   C.sub.2 H.sub.5                                                                    O  O  i-C.sub.3 H.sub.7                                Cl Cl H   H   H   i-C.sub.3 H.sub.7                                                                  O  O  i-C.sub.3 H.sub.7                                Cl Cl H   H   H   t-C.sub.4 H.sub.9                                                                  O  O  i-C.sub.3 H.sub.7                                Cl Cl H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                Cl H  6-F CH.sub.3                                                                          H   H    O  O  i-C.sub.3 H.sub.7                                Cl H  6-F H   CH.sub.3                                                                          H    O  O  i-C.sub.3 H.sub.7                                Cl H  6-F H   H   CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                Cl H  6-F H   H   C.sub.2 H.sub.5                                                                    O  O  i-C.sub.3 H.sub.7                                Cl H  6-F H   H   i-C.sub.3 H.sub.7                                                                  O  O  i-C.sub.3 H.sub.7                                Cl H  6-F H   H   t-C.sub.4 H.sub.9                                                                  O  O  i-C.sub.3 H.sub.7                                Cl H  6-F H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                Cl H  6-Cl                                                                              CH.sub.3                                                                          H   H    O  O  i-C.sub.3 H.sub.7                                Cl H  6-Cl                                                                              H   CH.sub.3                                                                          H    O  O  i-C.sub.3 H.sub.7                                Cl H  6-Cl                                                                              H   H   CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                Cl H  6-Cl                                                                              H   H   C.sub.2 H.sub.5                                                                    O  O  i-C.sub.3 H.sub.7                                Cl H  6-Cl                                                                              H   H   i-C.sub.3 H.sub.7                                                                  O  O  i-C.sub.3 H.sub.7                                Cl H  6-Cl                                                                              H   H   t-C.sub.4 H.sub.9                                                                  O  O  i-C.sub.3 H.sub.7                                Cl H  6-Cl                                                                              H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                          H   H    O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          H    O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   C.sub.2 H.sub.5                                                                    O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   i-C.sub.3 H.sub.7                                                                  O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   t-C.sub.4 H.sub.9                                                                  O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                          H   H    O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   CH.sub.3                                                                          H    O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   C.sub.2 H.sub.5                                                                    O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   i-C.sub.3 H.sub.7                                                                  O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   t-C.sub.4 H.sub.9                                                                  O  O  i-C.sub.3 H.sub.7                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O  i-C.sub.3 H.sub.7                                Cl Cl H   CH.sub.3                                                                          H   H    O  O  s-C.sub.4 H.sub.9                                Cl Cl H   H   CH.sub.3                                                                          H    O  O  s-C.sub.4 H.sub.9                                Cl Cl H   H   H   CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                Cl Cl H   H   H   C.sub.2 H.sub.5                                                                    O  O  s-C.sub.4 H.sub.9                                Cl Cl H   H   H   i-C.sub.3 H.sub.7                                                                  O  O  s-C.sub.4 H.sub.9                                Cl Cl H   H   H   t-C.sub.4 H.sub.9                                                                  O  O  s-C.sub.4 H.sub.9                                Cl Cl H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                Cl H  6-F CH.sub.3                                                                          H   H    O  O  s-C.sub.4 H.sub.9                                Cl H  6-F H   CH.sub.3                                                                          H    O  O  s-C.sub.4 H.sub.9                                Cl H  6-F H   H   CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                Cl H  6-F H   H   C.sub.2 H.sub.5                                                                    O  O  s-C.sub.4 H.sub.9                                Cl H  6-F H   H   i-C.sub.3 H.sub.7                                                                  O  O  s-C.sub.4 H.sub.9                                Cl H  6-F H   H   t-C.sub.4 H.sub.9                                                                  O  O  s-C.sub.4 H.sub.9                                Cl H  6-F H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                Cl H  6-Cl                                                                              CH.sub.3                                                                          H   H    O  O  s-C.sub.4 H.sub.9                                Cl H  6-Cl                                                                              H   CH.sub.3                                                                          H    O  O  s-C.sub.4 H.sub.9                                Cl H  6-Cl                                                                              H   H   CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                Cl H  6-Cl                                                                              H   H   C.sub.2 H.sub.5                                                                    O  O  s-C.sub.4 H.sub.9                                Cl H  6-Cl                                                                              H   H   i-C.sub.3 H.sub.7                                                                  O  O  s-C.sub.4 H.sub.9                                Cl H  6-Cl                                                                              H   H   t-C.sub.4 H.sub.9                                                                  O  O  s-C.sub.4 H.sub.9                                Cl H  6-Cl                                                                              H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                          H   H    O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          H    O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   C.sub.2 H.sub.5                                                                    O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   i-C.sub.3 H.sub.7                                                                  O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   t-C.sub.4 H.sub.9                                                                  O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   CH.sub.3                                                                          H    O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                          H   H    O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   C.sub.2 H.sub.5                                                                    O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   i-C.sub.3 H.sub.7                                                                  O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   t-C.sub.4 H.sub.9                                                                  O  O  s-C.sub.4 H.sub.9                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O  s-C.sub.4 H.sub.9                                Cl Cl H   CH.sub.3                                                                          H   H    O  O                                                   Cl Cl H   H   CH.sub.3                                                                          H    O  O                                                                                 ##STR66##                                       Cl Cl H   H   H   CH.sub.3                                                                           O  O                                                                                 ##STR67##                                       Cl Cl H   H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR68##                                       Cl Cl H   H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR69##                                       Cl Cl H   H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR70##                                       Cl Cl H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR71##                                       Cl H  6-F CH.sub.3                                                                          H   H    O  O                                                                                 ##STR72##                                       Cl H  6-F H   CH.sub.3                                                                          H    O  O                                                                                 ##STR73##                                       Cl H  6-F H   H   CH.sub.3                                                                           O  O                                                                                 ##STR74##                                       Cl H  6-F H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR75##                                       Cl H  6-F H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR76##                                       Cl H  6-F H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR77##                                       Cl H  6-F H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR78##                                       Cl H  6-Cl                                                                              CH.sub.3                                                                          H   H    O  O                                                                                 ##STR79##                                       Cl H  6-Cl                                                                              H   CH.sub.3                                                                          H    O  O                                                                                 ##STR80##                                       Cl H  6-Cl                                                                              H   H   CH.sub.3                                                                           O  O                                                                                 ##STR81##                                       Cl H  6-Cl                                                                              H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR82##                                       Cl H  6-Cl                                                                              H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR83##                                       Cl H  6-Cl                                                                              H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR84##                                       Cl H  6-Cl                                                                              H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR85##                                       CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                          H   H    O  O                                                                                 ##STR86##                                       CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          H    O  O                                                                                 ##STR87##                                       CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   CH.sub.3                                                                           O  O                                                                                 ##STR88##                                       CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR89##                                       CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR90##                                       CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR91##                                       CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR92##                                       CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                          H   H    O  O                                                                                 ##STR93##                                       CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   CH.sub.3                                                                          H    O  O                                                                                 ##STR94##                                       CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O                                                                                 ##STR95##                                       CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR96##                                       CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR97##                                       CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR98##                                       CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O                                                                                 ##STR99##                                       Cl Cl H   CH.sub.3                                                                          H   H    O  O                                                                                 ##STR100##                                      Cl Cl H   H   CH.sub.3                                                                          H    O  O                                                                                 ##STR101##                                      Cl Cl H   H   H   CH.sub.3                                                                           O  O                                                                                 ##STR102##                                      Cl Cl H   H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR103##                                      Cl Cl H   H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR104##                                      Cl Cl H   H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR105##                                      Cl Cl H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR106##                                      Cl H  6-F CH.sub.3                                                                          H   H    O  O                                                                                 ##STR107##                                      Cl H  6-F H   CH.sub.3                                                                          H    O  O                                                                                 ##STR108##                                      Cl H  6-F H   H   CH.sub.3                                                                           O  O                                                                                 ##STR109##                                      Cl H  6-F H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR110##                                      Cl H  6-F H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR111##                                      Cl H  6-F H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR112##                                      Cl H  6-F H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR113##                                      Cl H  6-Cl                                                                              CH.sub.3                                                                          H   H    O  O                                                                                 ##STR114##                                      Cl H  6-Cl                                                                              H   CH.sub.3                                                                          H    O  O                                                                                 ##STR115##                                      Cl H  6-Cl                                                                              H   H   CH.sub.3                                                                           O  O                                                                                 ##STR116##                                      Cl H  6-Cl                                                                              H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR117##                                      Cl H  6-Cl                                                                              H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR118##                                      Cl H  6-Cl                                                                              H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR119##                                      Cl H  6-Cl                                                                              H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR120##                                      CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                          H   H    O  O                                                                                 ##STR121##                                      CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          H    O  O                                                                                 ##STR122##                                      CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   CH.sub.3                                                                           O  O                                                                                 ##STR123##                                      CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR124##                                      CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR125##                                      CH.sub.3                                                                         CH.sub.3                                                                         H   H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR126##                                      CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                          CH.sub.3                                                                           O  O                                                                                 ##STR127##                                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                          H   H    O  O                                                                                 ##STR128##                                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   CH.sub.3                                                                          H    O  O                                                                                 ##STR129##                                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O                                                                                 ##STR130##                                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   C.sub.2 H.sub.5                                                                    O  O                                                                                 ##STR131##                                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   i-C.sub.3 H.sub.7                                                                  O  O                                                                                 ##STR132##                                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   t-C.sub.4 H.sub.9                                                                  O  O                                                                                 ##STR133##                                      CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.3                                                                           O  O                                                                                 ##STR134##                                      __________________________________________________________________________

If, according to process (A), ethylN-2,4-dichlorophenyl-acetyl-1-amino-4-ethylcyclohexane-carboxylate isused, the course of the process according to the invention can berepresented by the following equation: ##STR135##

If, according to process (B) variant α),3-(2,4,6-trimethylphenyl)-5,5-(3-methyl)-pentamethylene-pyrrolidine-2,4-dioneand pivaloyl chloride are used as starting substances, the course of theprocess according to the invention can be represented by the followingequation: ##STR136##

If, according to process B (variant β),3-(2,4,6-trimethylphenyl)-5,5-(tetramethyl)-dimethylene-pyrrolidine-2,4-dioneand acetic anhydride are used as starting compounds, the course of theprocess according to the invention can be represented by the followingequation: ##STR137##

If, according to process (C),3-(2,4,6-trimethylphenyl)-5,5-(3-methyl)-tetramethylene-pyrrolidine-2,4-dioneand ethoxyethyl chloroformate are used as starting compounds, the courseof the process according to the invention can be represented by thefollowing equation. ##STR138##

If, according to process (D.sub.α),3-(2,4,6-trimethylphenyl)-5.5-(4,4-dimethyl)-pentamethylene-pyrrolidine-2,4-dioneand mehyl chloromonothioformate are used as starting materials, thecourse of the reaction can be represented as follows: ##STR139##

If, according to process (D.sub.β),3-(2,4,6-trimethylphenyl-5,5-(4-methoxy)-pentmethylene-pyrrolidne-2,4-dione,carbon disulphide and methyl iodide are used as starting components, thecourse of the reaction can be represented as follows: ##STR140##

If, according to process (E),3-(2,4,6-trimethylphenyl)-5.5-(2-methyl)-pentamethylene-pyrrolidine-2,4-dioneand methanesulphonyl chloride are used as starting material, the courseof the reaction can be represented by the following equation: ##STR141##

If, according to process (F),3-(2,4-dimethylphenyl)-5.5-(3-methyl)-pentamethylene-pyrrolidine-2,4-dioneand 2,2,2-trifluoroethyl methanethiochlorophosphonate are used asstarting materials, the course of the reaction can be represented by theequation: ##STR142##

If, according to process (G),3-(2,4,6-trimethylphenyl)-5,5-(4-tert-butyl)-pentamethylene-pyrrolidine-2,4-dioneand NaOH are used as components, the course of the process according tothe invention can be represented by the following equation: ##STR143##

If, according to process (H.sub.α),3-(2,4,6-trimethylphenyl)-5,5-(2-methyl)-pentamethylene-pyrrolidine-2,4-dioneand ethyl isocyanate are used as starting materials, the course of thereaction can be represented by the following equation: ##STR144##

If, according to process (H.sub.β),3-(2,4,6-trimethylphenyl)-5,5-(3,4-dimethyl)pentamethylene-pyrrolidine-2,4-dioneand dimethylcarbamoyl chloride are used as starting materials, thecourse of the process can be represented by the following equation:##STR145##

The compounds of the formula (II) ##STR146## in which A, B, X, Y, Z, nand R⁸ have the abovementioned meaning, which are required as startingmaterials in processes (A) according to the invention,

are new.

Acyl-amino acid esters of the formula (II) are obtained, for example,when

amino acid derivatives of the formula (XIV) ##STR147## in which R^(9')represents hydrogen (XIVa) and alkyl (XIVb)

and

A and B have the abovementioned meaning

are acylated (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indien J.Chem 6, 341-5, 1968)- with phenylacetyl halides of the formula (XV)##STR148## in which X, Y, Z and n have the abovementioned meaning and

Hal represents chlorine or bromine

or when acylamino acids of the formula (IIa) ##STR149## in which A, B,X, Y, Z and n have the abovementioned meaning

and

R⁹ represents hydrogen

are esterified (Chem. Ind. (London) 1568 (1968)).

The substituted cyclohexylaminocarboxylic acids of the formula (XIVa)can generally be obtained in a Bucherer-Bergs reaction or by means ofStrecker synthesis and they are obtained in each case in variousisomeric forms. For example, the conditions of the Bucherer-Bergsreaction give mainly the isomers in which R and the carbamoyl group arepositioned equatorial (hereinafter termed β for the sake ofsimplicity)while the conditions of Strecker synthesis give mainly theisomers in which R and the aminogroup are positioned equatorial(hereinafter termed α for the sake of simplicity). ##STR150##

(L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, C. Jitrangeri, Can.J. Chem. 53, 3339 (1975).

Furthermore, the starting materials of the formula (II) ##STR151## inwhich A, B, X, Y, T, Z, n and R8 have the abovementioned meaning, whichare used in the above processes (A),

can be prepared when aminonitriles of the formula (XVI) ##STR152## inwhich A and B have the abovementioned meaning are reacted withphenylacetyl halides of the formula (XV) ##STR153## in which X, Y, Z andn have the abovementioned meaning and

Hal represents chorine or bromine,

to give compounds of the formula (XVII) ##STR154## in which A, B, X, Y,Z and n have the abovementioned meaning,

and these are subsequently subjected to alcoholysis in sulphuric acid.

The compounds of the formula (XVII) are also new.

In addition to the intermediates mentioned in the preparation examples,the following compounds of the formula (II) may be mentioned by way ofexample but not by way of limitation:

methylN-(2,4-dichlorphenylacetyl)-1-amino-2-methylcyclohexanecarboxylate,

methylN-(2,4-dichlorophenylacetyl)-1-amino-3-methylcyclohexanecarboxylate,

methylN-(2,4-dichlorophenylacetyl)-1-amino-4-methylcyclohexanecarboxylate,

methylN-(2,4-dichlorophenylacetyl)-1-amino-3,4-dimethylcyclohexanecarboxylate,

methylN-(2,4-dichlorophenylacetyl)-1-amino-4-ethylcyclohexanecarboxylate,

methylN-(2,4-dichlorophenylacetyl)-1-amino-4-isopropylcyclohexanecarboxylate,

methylN-(2,4-dichlorophenylacetyl)-1-amino-4-tert-butylcyclohexanecarboxylate,

methylN-(2,4-dichlorophenylacetyl)-1-amino-4-phenylcyclohexanecarboxylate,

methylN-(2,6-dichlorophenylacetyl)-1-amino-2-methylcyclohexanecarboxylate,

methylN-(2,6-dichlorophenylacetyl)-1-amino-3-methylcyclohexanecarboxylate,

methylN-(2,6-dichlorophenylacetyl)-1-amino-4-methylcyclohexanecarboxylate,

methylN-(2,6-dichlorophenylacetyl)-1-amino-3,4-dimethyl-cycl2,6-dichloropheate,

methylN-(2,6-dichlorophenylacetyl)-1-amino-4-ethylcyclohexanecarboxylate,

methylN-(2,6-dichlorophenylacetyl)-1-amino-4-isopropylcyclohexanecarboxylate,

methyl-(2,6-dichlorophenylacetyl)-1-amino-4-tert-butylcyclohexanecarboxylate,

methylN-(2,6-dichlorophenylacetyl)-1-amino-4-phenylcyclohexanecarboxylate,

methyl N-(2-chloro-6-fluoro-phenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylate,

methylN-(2-chloro-6-fluorophenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylate,

methylN-(2-chloro-6-fluorophenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylate,

methylN-(2-chloro-6-fluorophenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylate,

methylN-(2-chloro-6-fluorophenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylate,

methylN-(2-chloro-6-fluorophenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylate,

methylN-(2-chloro-6-fluorophenylacetyl)1-amino-4-tert-butyl-cyclohexanecarboxylate,

methylN-(2-chloro-6-fluorophenylacetyl)-1-amino-4-phenyl-cyclohexanecarboxylate,

methylN-(2,4,6-trimethylphenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylate,

methylN-(2,4,6-trimethylphenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylate,

methyl-(2,4,6-trimethylphenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylate,

methylN-(2,4,6-trimethylphenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylate,

methylN-(2,4,6-trimethylphenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylate,

methylN-(2,4,6-trimethylphenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylate

methylN-(2,4,6-trimethylphenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylate,

methylN-(2,4,6-trimethylphenylacetyl)-1-amino-4-phenyl-cylcohexanecarboxylate,

methylN-(2,4-dimethylphenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylate,

methylN-(2,4-dimethylphenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylate,

methylN-(2,4-dimethylphenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylate,

methylN-(2,4-dimethylphenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylate,

methylN-(2,4-dimethylphenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylate;

methylN-(2,4-dimethylphenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylate,

methylN-(2,4-dimethylphenylacetyl)-1-amino-4-phenyl-cyclohexanecarboxylate,

In addition to the intermediates mentioned in the preparation examples,the following compounds of the formula (IIa) may be mentioned by way ofexample but not by way of limitation:

N-(2,4-dichlorophenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylicacid,

N-(2,4-dichlorophenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylicacid,

N-(2,4-dichlorophenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylicacid,

N-(2,4-dichlorophenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylicacid,

N-(2,4-dichlorophenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylic acid,

N-(2,4-dichlorophenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylicacid,

N-(2,4-dichlorophenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylicacid,

N-(2,4-dichlorophenylacetyl)-1-amino-4-phenyl-cyclohexanecarboxylicacid,

N-(2,6-dichlorophenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylicacid,

N-(2,6-dichlorophenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylicacid,

N-(2,6-dichlorophenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylicacid,

N-(2,6-dichlorophenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylicacid,

N-(2,6-dichlorophenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylic acid,

N-(2,6-diclorophenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylicacid,

N-(2,6-dichlorophenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylicacid,

N-(2,6-dichlorophenylacetyl)-1-amino-4-phenyl-cyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-2-methylcyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-3-methylcyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-4-methylcyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-3,4-dimethylcyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylicacid,

N-(2-chloro-6-fluorophenylacetyl)-1-amino-4-phenyl-cyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-3,4-dimethylcyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-4-tert-butylcyclohexanecarboxylicacid,

N-(2,4,6-trimethylphenylacetyl)-1-amino-4-phenyl-cyclohexanecarboxylicacid,

N-(2,4-dimethylphenylacetyl)-1-amino-2-methyl-cyclohexanecarboxylicacid,

N-(2,4-dimethylphenylacetyl)-1-amino-3-methyl-cyclohexanecarboxylicacid,

N-(2,4-dimethylphenylacetyl)-1-amino-4-methyl-cyclohexanecarboxylicacid,

N-(2,4-dimethylphenylacetyl)-1-amino-3,4-dimethyl-cyclohexanecarboxylicacid,

N-(2,4-dimethylphenylacetyl)-1-amino-4-ethyl-cyclohexanecarboxylic acid,

N-(2,4-dimethylphenylacetyl)-1-amino-4-isopropyl-cyclohexanecarboxylicacid,

N-(2,4-dimethylphenylacetyl)-1-amino-4-tert-butyl-cyclohexanecarboxylicacid,

N-(2,4-dimethylphenylacetyl)-1-amino-4-phenyl-cyclohexanecarboxylicacid,

Compounds of the formula (IIa) can be obtained, for example, from thephenylacetyl halides of the formula (XV) and amino acids of the formula(XIVa) by the method of Schotten-Baumann (Organikum Laboratory Practicalin Organic Chemistry!, 9th Edition, 446 (1970) VEB Deutscher Verlag derWissenschaften, Berlin).

The acid halides of the formula (III), carboxylic anhydrides of theformula (IV), chloroformic esters or chloroformic thioesters of theformula (V), chloromonothioformic esters or chlorodithioformic esters ofthe formula (VI), alkyl halides of the formula (VII), sulphonylchlorides of the formula (VIII), phosphorus compounds of the formula(IX) and metal hydroxides or amines of the formula (X) and (XI) andisocyanates or carbomoyl chloride of the formula (XIII), all of whichare furthermore required as starting materials for carrying outprocesses (B), (C), (D), (E), (F), (G) and H according to the invention,are generally compounds of organic, or inorganic, chemistry.

Process (A) is characterised in that compounds of the formula (II) inwhich A, B, X, Y, Z, n and R⁸ have the abovementioned meaning aresubjected to an intramolecular condensation reaction in the presence ofbases.

Diluents which can be employed in process (A) according to the inventionare all inert organic solvents. The following can preferably be used:hydrocarbons such as toluene and xylene, furthermore ethers such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, andalso alcohols such as methanol, ethanol, propanol, isopropanol, butanol,iso-butanol and tert.-butanol.

Bases (deprotonating agents) which can be employed for carrying outprocess (A) according to the invention are all customary protonacceptors. The following can preferably be used: alkali metal oxides,alkali metal hydroxides, alkali metal carbonates, alkaline earth metaloxides, alkaline earth metal hydroxides and alkaline earth metalcarbonates such as sodium hydroxide, potassium hydroxide, magnesiumoxide, calcium oxide, sodium carbonate, potassium carbonate and calciumcarbonate, sodium carbonate, potassium carbonate and calcium carbonate,all of which can also be employed in the presence of phase transfercatalysts such as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 or TDA 1*). Alkali metals such assodium or potassium can also be used. Furthermore, alkali metal amides,alkali metal hydrides, alkaline earth metal amides and alkaline earthmetal hydrides such as sodium amide, sodium hydride and calcium hydride,and moreover also alkali metal alcoholates such as sodium methylate,sodium ethylate and potassium tert.-butylate, can also be employed.

When carrying out process (A) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 250° C.,preferably between 50° C. and 150° C.

Process (A) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (A) according to the invention, the reactantsof the formula (II) and the deprotonating bases are generally employedin approximately twice the equimolar amounts. However, it is possible touse one or the other component in a larger excess (up to 3 mol).

Process (Bα) is characterised in that compounds of the formula (Ia) arereacted with carboxylic halides of the

When the acid halides are used, then diluents which can be employed inprocess (Bα) according to the invention are all solvents which are inertto these compounds. The following can preferably be used: hydrocarbonssuch as benzine, benzene, toluene, xylene and tetralin, furthermorehalogenohydrocarbons such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketonessuch as acetone and methyl isopropyl ketone, furthermore ethers such asdiethyl ether, tetrahydrofuran and dioxane, in addition carboxylatessuch as ethyl acetate, and also strongly polar solvents such as dimethylsulphoxide and sulpholane. If the acid halide is sufficiently stable tohydrolysis, the reaction can also be carried out in the presence ofwater.

If the corresponding carboxylic acid halides are used, then acid-bindingagents which are suitable for the reaction in process (Bα) according tothe invention are all customary acid acceptors. The following canpreferably be used: tertiary amines such as triethylamine, pyridine,diazabiyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonene(DBN), Hunig base and N,N-dimethyl-aniline, furthermore alkaline earthmetal oxides such as magnesium oxide and calcium oxide, moreover alkalimetal carbonate and alkaline earth metal carbonates such as sodiumcarbonate, potassium carbonate and calcium carbonate, and also alkalimetal hydroxides such as sodium hydroxide and potassium hydroxide.

In process (Bα) according to the invention, too, the reactiontemperatures can also be varied within a substantial range whencarboxylic acid halides are used. In general, the process is carried outat temperatures between -20° C. and +150° C., preferably between 0° C.and 100° C.

When carrying out the process (Bα) according to the invention, thestarting materials of the formula (Ia) and the carboxylic acid halide ofthe formula (III) are generally used in approximately equivalentamounts. However, it is also possible to employ the carboxylic anhydridein a larger excess (up to 5 mol). Working-up is carried out by customarymethods.

Process (Bβ) is characterised in that compounds of the formula (Ia) arereacted with carboxylic acid hydrides of the formula (IV).

If, in process (Bβ), according to the invention, carboxylic anhydridesare used as reactant of the formula (IV), then diluents which canpreferably be used are those which are also preferably suitable whenacid halides are used. Apart from this, a carboxylic acid hydrideemployed in excess can also simultaneously act as a diluent.

When carrying out the process (Bβ) according to the invention, thereaction temperatures can also be varied within a substantial range whencarboxylic anhydrides are used. In general, the process is carried outat temperatures between -20° C. and +150° C., preferably between 0° C.and 100° C.

When carrying out the process according to the invention, the startingmaterials of the formula (Ia) and the carboxylic anhydride of theformula (IV) are generally employed in approximately equivalent amounts.However, it is also possible to employ the carboxylic anhydride in alarger excess (up to 5 mol). Working-up is carried out by customarymethods.

In general, a procedure is followed in which diluent and an excess ofcarboxylic anhydride as well as the carboxylic acid which forms areremoved by distillation or by washing with an organic solvent or withwater.

Process (C) is characterised in that compounds of the formula (Ia) arereacted with chloroformic esters or chloroformic thioesters of theformula (V).

If the corresponding chloroformic esters, or chloroformic thioesters,are used, then acid-binding agents which are suitable for the reactionin process (C) according to the invention are all customary acidacceptors. The following can preferably be used: tertiary amines such astriethylamine, pyridine, DABCO, DBU, DBA, Hunig base andN,N-dimethylaniline, furthermore alkaline earth metal oxides such asmagnesium oxide and calcium oxide, moreover alkali metal carbonates andalkaline earth metal carbonates such as sodium carbonate, potassiumcarbonate and calcium carbonate, as well as alkali metal hydroxides suchas sodium hydroxide and potassium hydroxide.

If the chloroformic esters, or chloroformic thioesters, are used, thendiluents which can be employed in process (C) according to the inventionare all solvents which are inert to these compounds. The following canpreferably be used: hydrocarbons such as benzine, benzene, toluene,xylene and tetralin, furthermore halogenohydrocarbons such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones such as acetone and methyl isopropylketone, furthermore ethers such as diethyl ether, tetrahydrofuran anddioxane, in addition carboxylates such as ethyl acetate, and alsostrongly polar solvents such as dimethyl sulphoxide and sulpholane.

If the chloroformic esters, or chloroformic thioesters, are used ascarboxylic acid derivatives of the formula (V), then the reactiontemperatures for carrying out process (C) according to the invention canbe varied within a substantial range. If the process is carried out inthe presence of a diluent and of an acid-binding agent, the reactiontemperatures are generally between -20° C. and +100° C. preferablybetween 0° C. and 50° C.

Process (C) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (C) according to the invention, the startingmaterials of the formula (Ia) and the corresponding chloroformic ester,or chloroformic thioester, of the formula (V) are generally used inapproximately equivalent amounts. However, it is also possible to employone or the other component in a larger excess (up to 2 mol). Working-upis then carried out by customary methods. In general, a procedure isfollowed in which the salts which have precipitated are removed and thereaction mixture which remains is concentrated by stripping off thediluent.

In preparation process (D), approximately one mol ofchloromonothioformic ester, or chlorodithioformic ester, of the formula(VI) is reacted per mole of starting compound of the formula (Ia) at 0°to 120° C., preferably at 20° to 60° C.

Suitable diluents which are optionally added are all inert polar organicsolvents such as ethers, amides, sulphones and sulphoxides.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide and dimethylsulphide are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound Ia isprepared by an addition of strong deprotonating agents such as, forexample, sodium hydride or potassium tertiary butylate, a furtheraddition of acid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases, sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine beingmentioned by way of example.

The reaction can be carried out under atmospheric pressure or increasedpressure, it is preferably carried out under atmospheric pressure.Working-up is carried out by customary methods.

In preparation process (D.sub.β), an aquimolar amount, or an excess, ofcarbon disulphide is added per mole of starting compound of the formula(Ia). This process is preferably carried out at temperatures from 0° to50° C. and, in particular, at 20° to 30° C.

It is frequently expedient to first prepare the corresponding salt fromthe compound of the formula (Ia) by adding a deprotonating agent (suchas, for example, potassium tertiary butylate or sodium hydride). Thecompound (Ia) is reacted with carbon disulphide until the formation ofthe intermediate is complete, for example after stirring at roomtemperature for several hours.

The product is further reacted with the alkyl halide of the formula(VII) at preferably 0° to 70° C. in particular at 20° to 50° C. At leastan aquimolar amount of alkyl halide is employed in this process.

The process is carried out at atmospheric pressure or under increasedpressure, preferably under atmospheric pressure.

Again, working-up is carried out by customary methods.

In preparation process (E), approximately one mol of sulphonyl chloride(VIII) is reacted per mole of starting compound of the formula (Ia) at-20° to 150° C., preferably at 11° to 70° C.

Suitable diluents which are optionally added are all inert polar organicsolvents such as ethers, amides, nitriles, sulphones, sulphoxides orhalogenated hydrocarbons such as methylene chloride.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide, dimethylsulphide and methyloene chloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound Ia isprepared by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), a further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases, sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine beingmentioned by way of example.

The reaction can be carried out under atmospheric pressure or underincreased pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

To obtain compounds of the structure (Ie) in preparation process (F), 1to 2, preferably 1 to 1.3 mol of the phosphorus compound of the formula(IX) are reacted per mole of the compound (Ia) at temperatures between-40° C. and 150° C., preferably between -10° and 110° C.

Suitable diluents which are optionally added are all inert polar organicsolvents such as ethers, amides, nitriles, alcohols, sulphides,sulphones, sulphoxides and the like.

Acetonitrile, dimethyl sulphoxide, tetrahydrofuran, dimethylformamideand methylene chloride are preferably employed.

Suitable acid-binding agents which are optionally added are customaryinorganic or organic bases such as hydroxides or carbonates. Exampleswhich may be mentioned are sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine.

The reaction can be carried out under atmospheric pressure or underincreased pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods of organicchemistry. The end products obtained are preferably purified bycrystallisation, chromatographic purification or so-called "incipientdistillation", i.e. removal of the volatile components in vacuo.

Process (G) is characterised in that compounds of the formula (Ia) arereacted with metal hydroxides (X) or amines (XI).

Diluents which can be employed in the process according to the inventionare, preferably, ethers such as tetrahydrofuran, dioxane, diethyl ether,or else alcohols such as methanol, ethanol, isopropanol, but also water.Process (G) according to the invention is generally carried out underatmospheric pressure. The reaction temperatures are generally between-20° C. and 100° C., preferably between 0° C. and 50° C.

In preparation process (H.sub.α), approximately 1 mol of isocyanate ofthe formula (XII) is reacted-per mole of starting compound of theformula (Ia) at 0° to 100° C., preferably at 20° to 50° C.

Suitable diluents which are optionally added are all inert organicsolvents such as ethers, amides, nitriles, sulphones or sulphoxides.

If appropriate, catalysts can be added to accelerate the reaction.Catalysts which can be employed very advantageously are organotincompounds such as, for example, dibutyltin dilaurate. The process ispreferably carried out under atmospheric pressure.

In preparation process (H.sub.β), approximately 1 mol of carbamoylchloride of the formula (XIII) is reacted per mole of starting compoundof the formula (Ia) at 0° to 150° C., preferably at 20° to 70° C.

Suitable diluents which are optionally added, are all inert polarorganic solvents such as ethers, amides, sulphones or sulphoxides.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound (Ia) isprepared by adding strong deprotonating agents (such as, for example,sodium hydride or potassium tertiary butylate), a further addition ofacid-binding agents can be dispensed with.

If acid-binding agents are employed, then suitable substances arecustomary inorganic or organic bases, sodium hydroxide, sodiumcarbonate, potassium carbonate, triethylamine or pyridine beingmentioned by way of example.

The reaction can be carried out under atmospheric pressure or underincreased pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

The active compounds are suitable for combating animal pests, preferablyarthropods and nematodes, in particular insects and arachnids, whichoccur in agriculture, in forests, in the protection of stored productsand of materials, and in the hygiene sector. They are active againstnormally sensitive and resistant species and against all or individualdevelopment stages. The above-mentioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp..

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp..

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp..

From the order of the Thysanoptera, for example, Hercino-thripsfemoralis and Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyaiopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. Psylla spp..

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelidesobtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsadecemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodeschrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilussurinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus,Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica,Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctusspp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbiumpsylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derusspp., Melolontha melolontha, Amphimallon solsti tialis and Costelytrazealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp..

From the order of the Arachnida, for example, Scorpo maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae., Eriophyes ribis,Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommaspp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp.,Sarcoptes spp., Tarsonemus spp., Byrobia praetiosa, Panonychus spp.,Tetranychus spp..

The active compounds according to the invention are distinguished by ahigher insecticidal and acaricidal activity.

They can be used particularly successfully for combating insects whichare harmful to plants such as, for example, against the larvae of themustard beetle (Phaedon cochleariae) or against the larvae of the greenrice cicada (Nephotettix cincticeps) against the caterpillars of thecabbage moth Phutella maculipennis.

The active compounds according to the invention can furthermore be usedas defoliants, desiccants, agents for destroying broad-leaved plantsand, especially, as weed-killers. By weeds, in the broadest sense, thereare to be understood all plants which grow in locations where they areundesired. Whether the substances according to the invention act astotal or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Arena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Stirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective combating of weedsin annual cultures.

The active compounds according to the invention are highly suitable forselectively combating monocotyledon weeds in dicotyledon cultures by thepre- and post-emergence methods. They can be employed highlysuccessfully for example in cotton or sugar beet for combating grassweeds.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkyl-naphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates, assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkyl-aryl polyglycol ethers, alkylsulphonates,alkyl sulphates, arylsulphonates as well as albumen hydrolysis products;as dispersing agents there are suitable: for example lignin-sulphitewaste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedye-stuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For combating weeds, the active compounds according to the invention, assuch or in the form of their formulations, can also be used as mixtureswith known herbicides, finished formulations or tank mixes beingpossible.

Suitable herbicides for the mixtures are known herbicides, such as, forexample,1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(1H,3H)-dione(AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea(METABENZTHIAZURON) for combating weeds in cereals;4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) forcombating weeds in sugar beet and4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one(METRIBUZIN) for combating weeds in soya beans. Mixtures with2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)-butyricacid (2,4-DB); 2,4-dichlorophenoxypropionic acid (2,4-DP);3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BENTAZONE);methyl5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX);3,5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL); 2-chloro-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino!-carbonyl-benzenesulphonamide(CHLORSULFURON); 2- 4-(2,4-dichlorophenoxy)-phenoxy!-propionic acid, itsmethyl ester or its ethyl ester (DICLOFOP-METHYL);4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); 2-4-(6-chloro-2-benzoxazolyl)-oxy!-phenoxy -propanoic acid, its methyl esteror its ethyl ester (FENOXAPROP);(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy!-acetic acid or its1-methylheptyl ester (FLUROXYPYR); methyl 2-4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidizol-2-yl!-4(5)-methylbenzoate(IMAZAMETHABENZ); 3,5-diiodo-4-hydroxybenzotrile (IOXYNIL);N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON);(2-methyl-4-chlorophenoxy)-acetic acid (MCPA);(4-chloro-2-methylphenoxy)-propionic acid (MCPP);N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET); 2-((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)-carbonyl!-amino!-sulphonyl-benzoic acid or its (METSULFURON);N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN);0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE);4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYN); 3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino!-carbonyl!-amino!-sulphonyl!-thiophene-2-carboxylicacid (THIAMETURON); are also possible. Surprisingly, some mixtures alsoshow a synergistic action.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 0.01 and 10 kg of active compound perhectare of soil surface, preferably between 0.05 and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES Example (Ia-1) ##STR155##

4.14 g (0.138 mol) of sodium hydride are suspended in 70 ml of absolutetoluene and the mixture is refluxed. 25.6 g (0.069 mol) of methylN-(2,4,6-trimethylphenylacetyl)-1-amino-4-t.-butyl-cyclohexanecarboxylatein 140 ml of absolute toluene are added dropwise and the mixture issubsequently refluxed until the reaction has ended (checked bythin-layer chromatography). After the mixture has cooled to roomtemperature, ethanol is added dropwise, with ice-cooling, until no morehydrogen evolves. The solvent is then evaporated, the residue is takenup in ethanol, and the mixture is stirred into approx. 10% strengthhydrochloric acid at 0°-20° C. The solid which has precipitated isfiltered off with suction and dried.

After recrystallisation from chloroform/hexane, 14.90 g (63% of theory)of3(2,4.,6-trimethylphenyl)-5,5-(4-t-butyl)-pentamethylene-pyrrolidine-2,4-dioneof melting point m.p.: >220° C. are obtained (β-isomer).

Example (Ia-2) ##STR156##

37.2 g (0.331 mol) of potassium tert.-butylate are heated at refluxtemperature in 100 ml of absolute tetrahydrofuran. 52 g (0.151 mol) ofmethylN-(2,4,6-trimethylphenylacetyl)-1-amino-4,4-dimethyl-cyclohexanecarboxylatein 510 ml of absolute toluene are added dropwise, and the mixture isrefluxed for 90 minutes. When the reaction has ended, the batch isbrought to room temperature, and 500 ml of water are added. The aqueousphase is separated off, and the toluene phase is extracted using 220 mlof water. The combined aqueous phases are washed with toluene andsubsequently treated with 50 ml of concentrated hydrochloric acid atroom temperature. The solid which has precipitated is filtered withsuction, washed and dried. To purify the crude product further, it issuspended in 300 ml of methyl tert.-butyl ether and subjected tofiltration suction. 44.9 g (95% of theory) of3-(2,4,6-trimethylphenyl)-5,5-(4,4-dimethyl)-pentamethylene-pyrrolidine-2,4-dioneof melting point m.p.:>220° C. are obtained.

The following end products of the formula (Ia) which are listed in Table4 are obtained analogously to Example (Ia-1) and (Ia-2) and followingthe general information in the description for the processes accordingto the invention, in the form of the α-isomer or the β-isomer:##STR157##

                                      TABLE 4                                     __________________________________________________________________________                                Physical                                          Ex. No.                                                                           X  Y  Z.sub.n                                                                           R.sub.a                                                                          R.sub.b                                                                          R.sub.c1                                                                           R.sub.c2                                                                         constant                                                                           Note                                         __________________________________________________________________________    (Ia-3)                                                                            Cl Cl H   CH.sub.3                                                                         H  H    H  146  αa                                     (Ia-4)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  H    H  >220 a                                            (Ia-5)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                           H  >220 α                                      (Ia-6)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H    H  217  α                                      (Ia-7)                                                                            Cl Cl H   H  CH.sub.3                                                                         CH.sub.3                                                                           H  130-140                                                                            α                                      (Ia-8)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         CH.sub.3                                                                           H  >220 α                                      (Ia-9)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                           H  190-198                                                                            α                                      (Ia-10)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H    H  120  β                                       (Ia-11)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                           H  >220 β                                       (Ia-12)                                                                           Cl Cl H   H  CH.sub.3                                                                         H    H  >220 α                                      (Ia-13)                                                                           Cl Cl H   H  CH.sub.3                                                                         H    H  207-209                                                                            β                                       (Ia-14)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  CH.sub.3                                                                         H    H  188-499                                                                            β                                       (Ia-15)                                                                           Cl Cl H   H  H  CH.sub.3                                                                           H  205-207                                                                            α                                      (Ia-16)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                    H  149-200                                                                            α                                      (Ia-17)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                    H  196-202                                                                            β                                       (Ia-18)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                    H  212-213                                                                            α                                      (Ia-19)                                                                           Cl Cl H   H  H  CH.sub.3                                                                           H  >220 β                                       (Ia-20)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                           H  >220 β                                       (Ia-21)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                    H  235  β                                       (Ia-22)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        --CH.sub.2 --                                                                       H    H  >220 α                                      (Ia-23)                                                                           Cl Cl H   --CH.sub.2 --                                                                       H    H  214-217                                                                            α                                      (Ia-24)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  --   -- 183-185                                                                            α                                      (Ia-25)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         --   -- >220 α                                      (Ia-26)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.11                                                                   H  >260 α                                      (Ia-27)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.11                                                                   H  252-253                                                                            β                                       (Ia-28)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.5                                                                    H  >230 α                                      (Ia-29)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  --(CH.sub.2).sub.5 --                                                                 >220 --                                           (Ia-30)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  i-C.sub.3 H.sub.7                                                                  H  239-240                                                                            α                                      (Ia-31)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  O--CH.sub.3                                                                        H  >220 α                                      (Ia-32)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  O--CH.sub.3                                                                        H  >220 β                                       (Ia-33)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  C.sub.2 H.sub.5                                                                    H  186  β                                       (Ia-34)                                                                           Cl Cl H   H  H  C.sub.3 H.sub.7                                                                    H  182  β                                       (Ia-35)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  C.sub.3 H.sub.7                                                                    H  197  β                                       (Ia-36)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.3 H.sub.7                                                                    H  206  β                                       (Ia-37)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  i-C.sub.3 H.sub.7                                                                  H  196-205                                                                            β                                       (Ia-38)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  i-C.sub.3 H.sub.7                                                                  H  214  β                                       __________________________________________________________________________

Example (Ib-1) ##STR158##

5.12 g (0.015 mol) of3-(2,4,6-trimethylphenyl)-5,5-(4-t.-butyl)-pentamethylene-pyrrolidine-2,4-dioneare dissolved in 60 ml of absolute dichloromethane, and 2.1 ml oftrimethylamine are added. 1.13 ml of acetyl chloride in 5 ml of absolutedichoromethane are added at 0° to 10° C. The end of the reaction isdetermined by thin-layer chromatography. The mixture is washedsubsequently twice with 100 ml portions of 0.5N sodium hydroxidesolution, and the organic phase is dried over magnesium sulphate. Theresidue which is obtained after the solvent has been evaporated isrecrystallised from ethyl acetate/n-hexane.

2 g(35% of theory) of3-(2,4,6-trimethylphenyl)-5,5-(4-t.-butyl)-pentamethylene-4-acetyloxy-.DELTA.3-pyrolin-2-oneof melting point m.p.:>220° C. are obtained. (β-isomer).

Example (Ib-2) ##STR159##

3-(2,4-dichlorphenyl)-5,5-(2-methyl)-pentamethylene-4-acetyloxy-Δ3-pyrrolin-2-oneof melting point m.p.: 138° C. (isomer mixture) is obtained analogouslyto Example (Ib-1).

The end products of the formula (Ib) listed below in Table 5 areobtained analogously to Example (Ib-1) and (Ib-2) and following thegeneral information in the description for the processes according tothe invention in the form of the α-isomer or the β-isomer. ##STR160##

                                      TABLE 5                                     __________________________________________________________________________                                        physical                                  Ex.                                 const.                                    No. X  Y  Z.sub.n                                                                           R.sub.a                                                                          R.sub.b                                                                          R.sub.c1                                                                          R.sub.c2                                                                         R.sup.1  mp.: °C.                                                                    Isomer                               __________________________________________________________________________    (Ib-3)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  H   H  CH.sub.3  218 α                              (Ib-4)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  CH.sub.3 >220°                                                                       α                              (Ib-5)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  H   H  t-C.sub.4 H.sub.9                                                                       180 α                              (Ib-6)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         CH.sub.3                                                                          H  i-C.sub.3 H.sub.7                                                                       215 α                              (Ib-7)                                                                            Cl Cl H   H  CH.sub.3                                                                         H   H  i-C.sub.3 H.sub.7                                                                       146-147                                                                           α                              (Ib-8)                                                                            Cl Cl H   H  CH.sub.3                                                                         H   H  CH.sub.3  191 α                              (Ib-9)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  CH.sub.3  214 α                              (Ib-10)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  i-C.sub.3 H.sub.7                                                                       221 α                              (Ib-11)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  CH.sub.3  220 β                               (Ib-12)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  CH.sub.3 >220 β                               (Ib-13)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  t-C.sub.4 H.sub.9                                                                       228 α                              (Ib-14)                                                                           Cl Cl H   H  CH.sub.3                                                                         H   H  CH.sub.3  217-218                                                                           β                               (Ib-15)                                                                           Cl Cl H   H  CH.sub.3                                                                         H   H  i-C.sub.3 H.sub.7                                                                       162-163                                                                           β                               (Ib-16)                                                                           Cl Cl H   H  CH.sub.3                                                                         H   H  t-C.sub.4 H.sub.9                                                                       188-190                                                                           β                               (Ib-17)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  CH.sub.3                                                                         H   H  CH.sub.3  218-220                                                                           β                               (Ib-18)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  CH.sub.3                                                                         H   H  i-C.sub.3 H.sub.7                                                                       148-150                                                                           β                               (Ib-19)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         CH.sub.3                                                                          H  CH.sub.3  204 α                              (Ib-20)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  i-C.sub.3 H.sub.7                                                                       173 α                              (Ib-21)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  t-C.sub.4 H.sub.9                                                                       122 α                              (Ib-22)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  CH.sub.3  234 α                              (Ib-23)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  i-C.sub.3 H.sub.7                                                                       166-167                                                                           α                              (Ib-24)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  t-C.sub.4 H.sub.9                                                                       201 α                              (Ib-25)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  i-C.sub.3 H.sub.7                                                                      >220 β                               (Ib-26)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  CH.sub.3  201-203                                                                           α                              (Ib-27)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  i-C.sub.3 H.sub.7                                                                       183-185                                                                           α                              (Ib-28)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  t-C.sub.4 H.sub.9                                                                       183-185                                                                           α                              (Ib-29)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  i-C.sub.3 H.sub.7                                                                       151-152                                                                           β                               (Ib-30)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H                                                                                          180 β                               (Ib-31)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H                                                                                 ##STR161##                                                                             170-176                                                                           β                               (Ib-32)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H                                                                                 ##STR162##                                                                             215 β                               (Ib-33)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                   H  CH.sub.3  201-202                                                                           α                              (Ib-34)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                   H  i-C.sub.3 H.sub.7                                                                       179-181                                                                           α                              (Ib-35)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  CH.sub.3  202-205                                                                           α                              (Ib-36)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  i-C.sub.3 H.sub.7                                                                       177-179                                                                           α                              (Ib-37)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  t-C.sub.4 H.sub.9                                                                       175-177                                                                           α                              (Ib-38)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  CH.sub.3  212-213                                                                           β                               (Ib-39)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  i-C.sub.3 H.sub.7                                                                       176-178                                                                           β                               (Ib-40)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  t-C.sub.4 H.sub.9                                                                       217-218                                                                           β                               (Ib-41)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  CH.sub.3  199-201                                                                           β                               (Ib-42)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  t-C.sub.4 H.sub.9                                                                       205-206                                                                           β                               (Ib-43)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.2                                                                            H   H  CH.sub.3  225-228                                                                           α                              (Ib-44)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.2                                                                            H   H  i-C.sub.3 H.sub.7                                                                       179-182                                                                           α                              (Ib-45)                                                                           Cl Cl H   CH.sub.2                                                                            H   H  i-C.sub.3 H.sub.7                                                                       177-179                                                                           α                              (Ib-46)                                                                           Cl Cl H   CH.sub.2                                                                            H   H  t-C.sub.4 H.sub.9                                                                       223-226                                                                           α                              (Ib-47)                                                                           Cl Cl H   CH.sub.2                                                                            H   H  CH.sub.3  233-235                                                                           α                              (Ib-48)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  --  -- CH.sub.3  210-213                                                                           α                              (Ib-49)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  --  -- i-C.sub.3 H.sub.7                                                                       169-171                                                                           α                              (Ib-50)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         --  -- CH.sub.3  188 α                              (Ib-51)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         --  -- i-C.sub.3 H.sub.7                                                                       164 α                              (Ib-52)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.11                                                                  H  CH.sub.3  222-224                                                                           α                              (Ib-53)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.11                                                                  H  i-C.sub.3 H.sub.7                                                                       161-163                                                                           α                              (Ib-54)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.5                                                                   H  CH.sub.3  224-225                                                                           α                              (Ib-55)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3 >220 --                                   (Ib-56)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          CH.sub.3                                                                         i-C.sub.3 H.sub.7                                                                       217-218                                                                           --                                   (Ib-57)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                      >220 --                                   (Ib-58)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  (CH.sub.2).sub.5                                                                     CH.sub.3 >220 --                                   (Ib-59)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  (CH.sub.2).sub.5                                                                     i-C.sub.3 H.sub.7                                                                       208-210                                                                           --                                   (Ib-60)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  i-C.sub.3 H.sub.7                                                                 H  CH.sub.3  193 α                              (Ib-61)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  i-C.sub.3 H.sub.7                                                                 H  i-C.sub.3 H.sub.7                                                                       177-179                                                                           α                              (Ib-62)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  i-C.sub.3 H.sub.7                                                                 H  t-C.sub.4 H.sub.9                                                                      >220 α                              (Ib-63)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  OCH.sub.3                                                                         H  CH.sub.3 >220 α                              (Ib-64)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  OCH.sub.3                                                                         H  i-C.sub.3 H.sub.7                                                                       181-182                                                                           α                              (Ib-65)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  OCH.sub.3                                                                         H  i-C.sub.3 H.sub.7                                                                       187-189                                                                           β                               (Ib-66)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  CH.sub.3  196 β                               (Ib-67)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  i-C.sub.3 H.sub.7                                                                       172 β                               __________________________________________________________________________

Example (Ic-1) ##STR163##

5.12 g (0.015 mol) of3-(2,4,6-trimethylphenyl)-5,5-(4-t.-butyl)-pentamethylene-pyrrolidine-2,4-dioneare dissolved in 60 ml of absolute dichloromethane and the solution istreated with 2.1 ml of triethylamine. 2.05 g of sec-butyl chloroformatein 5 ml of absolute dichloromethane are added at 0°-10° C., and stirringof the batch is continued at room temperature. The end of the reactionis determined by thin-layer chromatography. The batch is subsequentlywashed twice using 100 ml portions of 0.5N sodium hydroxide solution,and the organic phase is dried over magnesium sulphate. The residueobtained after evaporation of the solvent is recrystallised from ethylacetate/n-hexane.

4.4 g (66% of theory) of 0-(sec.-butyl)-0-3-(2,4,6-trimethylphenyl)-5,5-(4-t.-butyl)-pentamethylene-Δ3-pyrrolin-4-yl-2-one!carbonate of melting point m.p.: >220° C. (β-isomer).

Example (Ic-2) ##STR164##

0-(sec.-butyl -0-3-(2,46-trimethylphenyl)-5,5-(4-t.-butyl)-pentamethylene-Δ3-pyrrolin-4-yl-2-one!carboxylate of melting point m.p.: 170° C. is obtained analogously toExample (Ic-1) (isomer mixture)

The end products of the formula (Ic) listed below in Table 6 areobtained analogously to Examples (Ic-1) and (Ic-2) and following thegeneral information in the description of the process according to theinvention, as the α-isomer or the β-isomer. ##STR165##

                                      TABLE 6                                     __________________________________________________________________________    Ex.                                         Iso-                              No. X  Y  Z.sub.n                                                                           R.sub.a                                                                          R.sub.b                                                                          R.sub.c1                                                                          R.sub.c2                                                                         L  M  R.sub.2                                                                             mp.: °C.                                                                    mer                               __________________________________________________________________________    (Ic-3)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  H   H  O  O  C.sub.2 H.sub.5                                                                     167  α                           (Ic-4)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  H   H  O  O  sec.-C.sub.4 H.sub.9                                                                188  α                           (Ic-5)                                                                            Cl Cl H   H  CH.sub.3                                                                         H   H  O  O  C.sub.2 H.sub.5                                                                     168  α                           (Ic-6)                                                                            CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  O  O  sec.-C.sub.4 H.sub.9                                                                >220 β                            (Ic-7)                                                                            Cl Cl H   H  CH.sub.3                                                                         H   H  O  S  CH.sub.2 --C.sub.6 H.sub.5                                                          148-150                                                                            β                            (Ic-8)                                                                            Cl Cl H   H  CH.sub.3                                                                         H   H  O  S  CH.sub.2 --C.sub.6 H.sub.5                                                          141-143                                                                            α                           (Ic-9)                                                                            Cl Cl H   H  CH.sub.3                                                                         H   H  O  S  sec.-C.sub.4 H.sub.9                                                                134-136                                                                            α                           (Ic-10)                                                                           Cl Cl H   H  CH.sub.3                                                                         H   H  O  S  i-C.sub.3 H.sub.7                                                                   77-79                                                                              α                           (Ic-11)                                                                           Cl Cl H   H  CH.sub.3                                                                         H   H  O  O  sec.-C.sub.4 H.sub.9                                                                133  α                           (Ic-12)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  O  O  C.sub.2 H.sub.5                                                                     194  α                           (Ic-13)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  O  O  sec.-C.sub.4 H.sub.9                                                                192  α                           (Ic-14)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  O  O  C.sub.2 H.sub.5                                                                     190-191                                                                            β                            (Ic-15)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         H   H  O  O  sec.-C.sub.4 H.sub.9                                                                >220 β                            (Ic-16)                                                                           Cl Cl H   H  CH.sub.3                                                                         H   H  O  O  C.sub.2 H.sub.5                                                                     202-203                                                                            β                            (Ic-17)                                                                           Cl Cl H   H  CH.sub.3                                                                         H   H  O  O  sec.-C.sub.4 H.sub.9                                                                179-180                                                                            β                            (Ic-18)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  CH.sub.3                                                                         H   H  O  O  C.sub.2 H.sub.5                                                                     165-166                                                                            β                            (Ic-19)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  CH.sub.3                                                                         H   H  O  O  sec.-C.sub.4 H.sub.9                                                                169-171                                                                            β                            (Ic-20)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         CH.sub.3                                                                          H  O  O  C.sub.2 H.sub.5                                                                     209  α                           (Ic-21)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         CH.sub.3                                                                          H  O  O  sec.-C.sub.4 H.sub.9                                                                171  α                           (Ic-22)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  O  O  C.sub.2 H.sub.5                                                                     151  α                           (Ic-23)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  O  O  sec.-C.sub.4 H.sub.9                                                                144  α                           (Ic-24)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  O  O  C.sub.2 H.sub.5                                                                     >220 β                            (Ic-25)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  O  O  C.sub.2 H.sub.5                                                                     170-173                                                                            α                           (Ic-26)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  O  O  sec.-C.sub.4 H.sub.9                                                                146-148                                                                            α                           (Ic-27)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                   H  O  O  C.sub.2 H.sub.5                                                                     166-168                                                                            α                           (Ic-28)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                   H  O  O  sec.-C.sub.4 H.sub.9                                                                199-203                                                                            α                           (Ic-29)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  O  O  C.sub.2 H.sub.5                                                                     188-190                                                                            α                           (Ic-30)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  O  O  sec.-C.sub.4 H.sub.9                                                                171-173                                                                            α                           (Ic-31)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  O  O  C.sub.2 H.sub.5                                                                     197-198                                                                            β                            (Ic-32)                                                                           Cl Cl H   H  H  CH.sub.3                                                                          H  O  O  sec.-C.sub.4 H.sub.9                                                                227-228                                                                            α                           (Ic-33)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  O  O  i-C.sub.3 H.sub.7                                                                   202-204                                                                            β                            (Ic-34)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  O  O  C.sub.2 H.sub.5                                                                     193-194                                                                            β                            (Ic-35)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H  H  CH.sub.3                                                                          H  O  O  sec.-C.sub.4 H.sub.9                                                                168-169                                                                            β                            (Ic-36)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  O  O  CH.sub.3                                                                            206  β                            (Ic-37)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          H  O  O  i-C.sub.3 H.sub.7                                                                   >220 β                            (Ic-38)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        --CH.sub.2 --                                                                       H   H  O  O  C.sub.2 H.sub.5                                                                     183-186                                                                            α                           (Ic-39)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        --CH.sub.2 --                                                                       H   H  O  O  sec.-C.sub.4 H.sub.9                                                                159-161                                                                            α                           (Ic-40)                                                                           Cl Cl H   --CH.sub.2 --                                                                       H   H  O  O  C.sub.2 H.sub.5                                                                     153-155                                                                            α                           (Ic-41)                                                                           Cl Cl H   --CH.sub.2 --                                                                       H   H  O  O  sec.-C.sub.4 H.sub.9                                                                155-157                                                                            α                           (Ic-42)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  --  -- O  O  C.sub.2 H.sub.5                                                                     173-176                                                                            α                           (Ic-43)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         H  --  -- O  O  sec.-C.sub.4 H.sub.9                                                                186-189                                                                            α                           (Ic-44)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         --  -- O  O  C.sub.2 H.sub.5                                                                     194  α                           (Ic-45)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  CH.sub.3                                                                         --  -- O  O  sec.-C.sub.4 H.sub.9                                                                187  α                           (Ic-46)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.11                                                                  H  O  O  C.sub.2 H.sub.5                                                                     155-156                                                                            α                           (Ic-47)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.11                                                                  H  O  O  sec.-C.sub.4 H.sub.9                                                                185-186                                                                            α                           (Ic-48)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.5                                                                   H  O  O  C.sub.2 H.sub.5                                                                     225-226                                                                            α                           (Ic-49)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.6 H.sub.5                                                                   H  O  O  sec.-C.sub.4 H.sub.9                                                                109-199                                                                            α                           (Ic-50)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          CH.sub.3                                                                         O  O  C.sub.2 H.sub.5                                                                     >220 --                                (Ic-51)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  CH.sub.3                                                                          CH.sub.3                                                                         O  O  sec.-C.sub.4 H.sub.9                                                                220-221                                                                            --                                (Ic-52)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  --(CH.sub.2)5--                                                                      O  O  C.sub.2 H.sub.5                                                                     227-229                                                                            --                                (Ic-53)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  --(CH.sub.2)5--                                                                      O  O  sec.-C.sub.4 H.sub.9                                                                206-208                                                                            --                                (Ic-54)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  i-C.sub.3 H.sub.7                                                                 H  O  O  C.sub.2 H.sub.5                                                                     143  α                           (Ic-55)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  i-C.sub.3 H.sub.7                                                                 H  O  O  sec.-C.sub.4 H.sub.9                                                                177-179                                                                            α                           (Ic-56)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  OCH.sub.3                                                                         H  O  O  C.sub.2 H.sub.5                                                                     182  α                           (Ic-57)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  OCH.sub.3                                                                         H  O  O  C.sub.2 H.sub.5                                                                     154  β                            (Ic-58)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                   H  O  O  C.sub.2 H.sub.5                                                                     236  β                            (Ic-59)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H  H  C.sub.2 H.sub.5                                                                   H  O  O  sec.-C.sub.4 H.sub.9                                                                179  β                            (Ic-60)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  O  O  C.sub.2 H.sub.5                                                                     204  β                            (Ic-61)                                                                           Cl Cl H   H  H  C.sub.2 H.sub.5                                                                   H  O  O  sec.-C.sub.4 H.sub.9                                                                198  β                            __________________________________________________________________________

Example (Id-1) ##STR166##

5.99 g (0.02 mol)3-(2,4,6-trimethylphenyl)-5,5-(4-methyl)-pentamethylene-pyrrolidine-2,4-dioneare dissolved in 70 ml of absolute dichloromethane and the solution istreated with 2.8 ml of triethylamine. 2.29 g of methane sulphonylchloride in 5 ml of absolute dichloromethane are added dropwise at 0° C.to 10° C. The end of the reaction is determined by thin-layerchromatography. The mixture is subsequently washed twice using 200 mlportions of 0.5N sodium hydroxide solution and the organic phase isdried over magnesium sulphate. After the solvent has been removed andthe residue has been suspended in ethyl acetate, 3.1 g (41% of theory)of3-(2,4,6-trimethylphenyl-5,5-(4-methyl)-pentamethylene-4-methylsulphonyloxy-Δ3-pyrrolin-2-oneof melting point m.p.: 205°-206° C. are obtained. (α-isomer)

Example (Ie-1) (α-Isomer) ##STR167##

2 g (6,2 mmol)3-(2,4-dichlorphenyl)-5,5-(3-methyl)-pentamethylen-pyrrolidin-2,4-dionare suspended in 20 ml of absolute tetrahydrofurane and treated with 1ml of triethylamine. After addition of 1,5 g (7 mmol) ofmethyl-sec-butylthiophoshonic-acidchloride the mixture is stirredovernight. The solvent is evaporated and the residue separatedchromatographically with cyclohexane/ethylacetate 2:1 on silicagel. 1.7g (37 % of theory) of the above mentioned compound (α-isomer, meltingpoint 69 ° C.) are obtained.

Example (If-1) ##STR168##

2.99 g (10mmol)3-(2,4-6-trimethylphenyl)-5,5-(4-methyl)-pentamethylen-pyrrolidin-2,4-dionare suspended in 40 ml of absolute methylenchloride. After addition of6,24 g tetrabutylammoniumhydroxide (40% aqueous solution) the mixture isstirred for minutes, the solvent is evaporated and the residuecrystallized with diisopropylether. 5.1 g (94% of theory) of the abovementioned compound (melting point 125° C., β-isomer) are obtained.

Example (If-2) ##STR169##

Analogously compound If-2 of melting point 110 ° C. is obtained.

Example (Ig-1) ##STR170##

5.99 g (0.02 mol) of3-(2,4,6-trimethylphenyl)-5,5-(4-methyl)-pentamethylene-pyrrolidine-2,4-dioneare dissolved in 70 ml of absolute dichloromethane and the solution istreated with 2.8 ml of triethylamine. 2.34 ml of morpholinecarbamoylchloride in 5 ml of dichloromethane are added at 0° to 10° C. andstirring of the batch is continued at room temperature until, accordingto check by thin-layer chromatography, the reaction has ended. Themixture is then washed twice using 200 ml portions of 0.5N sodiumhydroxide solution and the organic phase is dried over magnesiumsulphate. After the solvent has been evaporated and the residuesuspended in ethyl acetate, 2.3 g (28% of theory) of3-(2,4,6-trimethylphenyl)-5,5-(4-methyl)-pentamethylene-4-(morpholinecarbmoyl)-Δ3-pyrrolin-2-one of melting point m.p.: 197°-198° C. areobtained. (α-isomer).

Example (Ig-2)

Analogously3-(2,4,6-trimethylphenyl)-5,5-(4-methyl)pentamethylene-4-(morpholincarbamoyl)-Δ3-pyrrolin-2-on(melting point 189°-193° C.); β-isomer) are obtained.

Analogously are obtained:

                                      TABLE 7                                     __________________________________________________________________________    Ex                                  mp iso-                                   Nr.:                                                                             X  Y  Zn  R.sub.a                                                                         R.sub.b                                                                         R.sub.c1                                                                         R.sub.c2                                                                         L   R.sup.7                                                                           R.sup.8                                                                            °C.                                                                       mer                                    __________________________________________________________________________    (Ig-3)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H H CH.sub.3                                                                         H  O --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2                                                 >220                                                                             β                                 (Ig-4)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         H   H H CH.sub.3                                                                         H  O   CH.sub.3                                                                          CH.sub.3                                                                           >220                                                                             β                                 (Ig-5)                                                                           CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        H H CH.sub.3                                                                         CH.sub.3                                                                         O --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2                                                 167                                                                              --                                     __________________________________________________________________________

Preparation of the starting compounds

Example (II-1) ##STR171##

29.1 g (0.117 mol) of 4-(t-butyl)-methyl1-amino-1-cyclohexanecarboxylate hydrochloride are dissolved in 300 mlof tetrahydorfuran and the solution is treated with 34.4 ml (0.246 mol)of triethylamine. 23 g of mesityleneacetyl chloride in 20 ml of absolutetetrahydrofuran are added dropwise at 0° to 10° C. and stirring off thebatch is continued at room temperature. The end of the reaction isdetermined by thin-layer chromatography. The batch is stirred into 0.5 lof ice-water with 100 ml of 1N hydrochloric acid, and the mixture isextracted using dichloromethane. After the mixture has been washed withsodium hydrogen carbonate solution and after the organic phase has beendried, the solvent is stripped off. The crude product is recrystallisedfrom toluene/n-hexane. 25.6 g (59% of theory) of methylN-(2,4,6-tri-methylphenylacetyl)-1-amino-4.tert.-butyl-cyclohexane-carboxylateof melting point m.p.: 153°-154° C. (β-isomer) are obtained.

Example (II-2) ##STR172##

To 148 g (1.52 mol) of conc. sulphuric acid is added dropwise a solutionof 90.9 g (0.30 mol)N-(2,4,6-trimethylphenylacetyl)-4-methyl-1-amino-cyclohexane-nitrile in600 ml methylene chloride at a temperatur of 30°-40° C. After 2 h 212 mlof abs. methanol are added dropwise at 40° C. and the mixture is stirredfor 6 h at 40°-70° C.

Then the reaction mixture is poured into ice water and extracted withmethylene chloride. The organic phase is washed with aequous NaHCO₃,dried and evaporated. The product is purified by recristallisation fromtoluene/n-hexane.

Yield: 73.9 g (73% of theory) of methylN-(2,4,6-trimethylphenyl-acetyl)-4-methyl-1-amino-cyclohexanecarboxylateof melting point m.p.: 146° C.

The starting compounds of the formula (II) listed below in Table 7 areobtained analogously to Example (II-1) and following the generalinformation in the description for the processes according to theinvention, in the form of isomer mixtures. ##STR173##

                                      TABLE 8                                     __________________________________________________________________________    Ex.                           phys. const.                                                                        Iso-                                      No. R.sub.a                                                                          R.sub.b                                                                          R.sub.c1                                                                          R.sub.c2                                                                         X  Y  Z.sub.n                                                                           R.sup.8                                                                          mp.: °C.                                                                     mer                                       __________________________________________________________________________    (II-2)                                                                            H  H  CH.sub.3                                                                          H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         146   α                                   (II-3)                                                                            H  H  CH.sub.3                                                                          H  Cl Cl H   CH.sub.3                                                                         118   α                                   (II-4)                                                                            H  H  CH.sub.3                                                                          H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         149-151                                                                             β                                    (II-5)                                                                            CH.sub.3                                                                         H  H   H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         103-104                                                                             α                                   (II-6)                                                                            CH.sub.3                                                                         H  H   H  Cl Cl H   CH.sub.3                                                                         156   α                                   (II-7)                                                                            H  CH.sub.3                                                                         H   H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         123-124                                                                             β                                    (II-8)                                                                            H  CH.sub.3                                                                         H   H  Cl Cl H   CH.sub.3                                                                         144   α                                   (II-9)                                                                            H  H  CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         142   --                                        (II-10)                                                                           H  CH.sub.3                                                                         H   H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         160   α                                   (II-11)                                                                           H  H  CH.sub.3                                                                          H  CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                         127-128                                                                             α                                   (II-12)                                                                           H  CH.sub.3                                                                         CH.sub.3                                                                          H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         147   α                                   (II-13)                                                                           H  CH.sub.3                                                                         CH.sub.3                                                                          H  Cl Cl H   CH.sub.3                                                                         138   α                                   (II-14)                                                                           H  H  i-C.sub.3 H.sub.7                                                                 H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         137-139                                                                             α                                   (II-15)                                                                           H  H  C.sub.2 H.sub.5                                                                   H  Cl Cl H   CH.sub.3                                                                         103-105                                                                             α                                   (II-16)                                                                           H  H  C.sub.2 H.sub.5                                                                   H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         144-145                                                                             α                                   (II-17)                                                                           H  H  C.sub.2 H.sub.5                                                                   H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         129-130                                                                             β                                    (II-18)                                                                           H  H  OCH.sub.3                                                                         H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         116-118                                                                             α                                   (II-19)                                                                           H  H  C.sub.6 H.sub.11                                                                  H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         208-210                                                                             α                                   (II-20)                                                                           H  H  C.sub.6 H.sub.5                                                                   H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         207   α                                   (II-21)                                                                           H  H  --(CH.sub.2).sub.5 --                                                                CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         153-154                                                                             --                                        (II-22)                                                                           H  CH.sub.3                                                                         H   H  Cl Cl H   CH.sub.3                                                                         147-148                                                                             β                                    (II-23)                                                                           H  H  CH.sub.3                                                                          H  Cl Cl H   CH.sub.3                                                                         151-152                                                                             β                                    (II-24)                                                                           H  H  CH.sub.3                                                                          H  CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                         123-124                                                                             β                                    (II-25)                                                                           H  CH.sub.3                                                                         H   H  CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                         131   β                                    (II-26)                                                                           H  H  C.sub.2 H.sub.5                                                                   H  Cl Cl H   CH.sub.3                                                                         106   β                                    (II-27)                                                                           H  CH.sub.3                                                                         --  -- CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         83-85 α                                   (II-28)                                                                           CH.sub.3                                                                         H  --  -- CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         107-108                                                                             α                                   (II-29)                                                                           H  H  C.sub.2 H.sub.5                                                                   H  CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                         105   β                                    (II-30)                                                                           H  H  C.sub.3 H.sub.7                                                                   H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         155   β                                    (II-31)                                                                           H  H  C.sub.3 H.sub.7                                                                   H  CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                         131   β                                    (II-32)                                                                           H  H  C.sub.3 H.sub.7                                                                   H        H   CH.sub.3                                                                         106   β                                    (II-33)                                                                           H  H  i-C.sub.3 H.sub.7                                                                 H  CH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         145   β                                    (II-34)                                                                           H  H  i-C.sub.3 H.sub.7                                                                 H  CH.sub.3                                                                         CH.sub.3                                                                         H   CH.sub.3                                                                         118   β                                    __________________________________________________________________________

Examples for the preparation of the starting compounds of the formulaXVII: Example XVII-1 ##STR174##

To 40 g (0.2 mol) of 1-amino-4-phenyl-cyclohexanecarboxylic acid nitrileand 28 ml (0.2 mol) of triethylamine in 450 ml of absolutetetrahydrofuran there are added dropwise with stirring at 0° C. to 10°C. 39.3 g (0.2 mol) of mesityleneacetyl chloride (compare, for example,Tetrahedron 31, 2691-2694 1975!) in 40 ml of absolute tetrahydrofuran,and, when the addition has ended, the mixture is stirred at roomtemperature until starting material can no longer be detected in athin-layer chromatogram. For working-up, the reaction mixture is addedwith stirring to a mixture of 1000 ml of ice-water and 200 ml of 1Nhydrochloric acid, solid which has precipitated is filtered off withsuction, the residue is dissolved in dichloromethane, the aqueous phaseis separated, the organic phase is dried over magnesium sulphate and thesolvent is removed in vacuo. 65 g (91% of theory) ofN-(2,4,6-trimethylphenyl-acetyl-4-phenylcyclohexanecarboxylic nitrile ofmelting point 235°-238° C.) are obtained.

The following compounds XVII are obtained analogously and following thegeneral information on the preparation: ##STR175##

                  TABLE 9                                                         ______________________________________                                                                                        mp.:                          Ex. No.                                                                              R.sub.a                                                                              R.sub.b                                                                              R.sub.c1                                                                            R.sub.c2                                                                           X    Y    Z.sub.n                                                                             °C.                    ______________________________________                                        XVII-2 CH.sub.3                                                                             H      H     H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          183-                                                                          184                           XVII-3 CH.sub.3                                                                             H      H     H    Cl   Cl   H     153                           XVII-4 H      H      CH.sub.3                                                                            H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          202                           XVII-5 H      H      CH.sub.3                                                                            H    Cl   Cl   H     203                           XVII-6 H      CH.sub.3                                                                             H     H    Cl   Cl   H     189                           XVII-7 H      CH.sub.3                                                                             H     H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          176                           XVII-8 H      CH.sub.3                                                                             CH.sub.3                                                                            H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          174                           XVII-9 H      CH.sub.3                                                                             CH.sub.3                                                                            H    Cl   Cl   H     153                           XVII-10                                                                              H      H      CH.sub.3                                                                            H    CH.sub.3                                                                           CH.sub.3                                                                           H     198                           XVII-11                                                                              H      H      i-C.sub.3 H.sub.7                                                                   H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          204-                                                                          206                           XVII-12                                                                              H      H      C.sub.2 H.sub.5                                                                     H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          185                           XVII-13                                                                              H      H      C.sub.2 H.sub.5                                                                     H    Cl   Cl   H     194                           XVII-14                                                                              H      H      CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          190-                                                                          192                           XVII-15                                                                              H      H      OCH.sub.3                                                                           H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          159-                                                                          160                           XVII-16                                                                              H      H      C.sub.6 H.sub.11                                                                    H    CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          208                           XVII-17                                                                              H      H      --(CH.sub.2).sub.5 --                                                                  CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          198-                                                                          201                             XVII-18                                                                              H      CH.sub.3                                                                             --    --   CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          139                           XVII-19                                                                              CH.sub.3                                                                             H      --    --   CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                          142                           ______________________________________                                    

Example A

Phaedon larvae test

Solvent: 7 parts by weight of diemethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae), while theleaves are still moist.

After the specified period of time, the destruction in % is determined.100% means that all the beetle larvae have been killed; 0% means thatnone of the beetle larvae have been killed.

In this test, a superior activity compared with the prior art is shown,for example, for the following compounds of the preparation examples:(Ia-10), (Ia-11), (Ib-11), (Ib-12), (Ig-1).

Example B

Plutella test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with caterpillars of the diamond-back moth (Plutellamaculipennis) while the leaves are still moist.

After the specified period of time, the destruction in % is determined.100% means that all the caterpillars have been killed; 0% means thatnone of the caterpillars have been killed.

In this test, a superior activity compared with the prior art is shown,for example, for the following compounds of the preparation examples:(Ia-10), (Ia-11), (Ib-12), (Ig-1).

Example C

Nephotettix test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with larvae of the green rice cicada (Nephotettix cincticeps)while the leaves are still moist.

After the specified period of time, the destruction in % is determined.100% means that all the cicadas have been killed; 0% means that none ofthe cicadas have been killed.

In this test, a superior activity compared with the prior art is shown,for example, for the following compounds of the preparation examples:(Ia-10), (Ia-11), (Ib-11), (Ib-12) (Ig-1).

Example D

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the cencentrate is diluted with waterto the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control. The figuresdenote:

0%=no action (like untreated control)

100%=total destruction

A clearly superior activity and crop plant selectivity compared with theprior art is shown, in this test, for example by the compounds ofpreparation example: (Ia-10), (Ia-11), (Ib-12), (Ib-11), (Ic-6).

Example E

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. After threeweeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control. The figuresdenote:

0%=no action (like untreated control)

100%=total destruction

A clearly superior activity and crop plant selectivity compared with theprior art is shown, in this test, for example by the compounds ofpreparation example: (Ia-10), (Ia-11), (Ib-11), (Ib-12).

We claim:
 1. A compound of the formula ##STR176## in which A and Btogether with the carbon atom to which they are bonded represent asubstituted cycle,X represents alkyl, halogen or alkoxy, Y representshydrogen, alkyl, halogen, alkoxy or halogenoalkyl, Z represents alkyl,halogen or alkoxy, n represents 0, 1, 2 or 3, and R⁸ represents alkyl.2. Process for the preparation of the compounds of the formula (II),according to claim 1 characterized in that amino acid derivatives of theformula (XIV) ##STR177## in which R^(9') represents hydrogen (XIVa) andalkyl (XIVb) andA and B have the meaning given in claim 1 are acylatedwith phenylacetyl halides of the formula (XV) ##STR178## in which X, Y,Z and n have the meaning given in claim 1 and HAL represents chlorine orbromine or acylamine acids of the formula (IIa) ##STR179## in which A,B, X, Y, Z and n have the meaning given in claim 1 and R^(9') representshydrogen are esterfied, or aminonitriles of the formula (XVI) ##STR180##in which A and B have the abovementioned meaning are reacted withphenylacetyl halides of the formula (XV) ##STR181## in which X, Y, Z andn have the abovementioned meaning and Hal represents chlorine or bromineto give compounds of the formula (XVII) ##STR182## in which A, B, X, Y,Z and n have the abovementioned meaning and these compounds aresubsequently subjected to alcoholysis in sulphuric acid.
 3. The compoundaccording to claim 1 in whichA, B and the carbon atom to which they arebonded represent a C₃ -C₆ -spirocycle which can be monosubstituted orpolysubstituted by C₁ -C₆ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₃ -haloalkyl,C₁ -C₄ -alkoxy, C₁ -C₄ -thioalkyl, fluorine, chlorine or phenyl, or A, Band the carbon atom to which they are bonded represent a C₃ -C₆-spirocycle which is substituted by an alkylenediyl group which isoptionally interrupted by one or two oxygen or sulphur atoms or by analkylenedioxyl or an alkylenedithiooxyl group which, together with thecarbon atom to which it is bonded, forms a further five- toseven-membered spirocycle, or A, B and the carbon atom to which they arebonded represent a C₃ -C₆ -spirocycle in which two substituents togetherwith the C-atoms to which they are bonded represent a saturated orunsaturated carbocyle which is substituted by alkyl(C₁ -C₃), alkoxy(C₁-C₃), or fluorine, chlorine or bromine and which is optionallyinterrupted by oxygen or sulphur atom, X represents C₁ -C₄ -alkyl,halogen or C₁ -C₄ -alkoxy, Y represents hydrogen, methyl, ethyl, propyl,i-propyl, butyl, i-butyl, fluorine, chlorine, bromine, methoxy, ethoxyor trifluoromethyl, Z represents methyl, ethyl, prapyl, i-propyl, butyl,i-butyl, tert.-butyl, fluorine, chlorine, bromine, methoxy or ethoxy,represents 0, 1 or
 2. 4. The compound according to claim 1, in whichA, Band the carbon atom to which they are bonded represent a C₃ -C₆-spirocycle which can be at least monosubstituted or polysubstituted bymethyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec.-butyl,tert,-butyl, cyclohexyl, trifluoromethyl, methoxy, methylthio, fluorine,chlorine or phenyl, or A, B and the carbon atom to which they are bondedrepresent a C₃ -C₆ -spirocycle which is substituted by an alkylenediylgroup which is optionally interrupted by an oxygen or sulphur atom or byan alkylenedioxyl group which group, together with the carbon atom towhich it is bonded, forms a further five- to seven-membered spirocycle,A, B and the carbon atom to which they are bonded represent a C₃ -C₆-spirocycle in which two substituents together with the carbon atoms towhich they are bonded represent a saturated or unsaturated five- orsix-membered cycle, which is optionally interrupted by oxygen orsulphur, X represents methyl, ethyl, propyl, 2-propyl, fluorine,chlorine, bromine, methoxy or ethoxy, Y represents hydrogen, methyl,ethyl, propyl, i-propyl, butyl, i-butyl, tert.-butyl, fluorine,chlorine, bromine, methoxy, ethoxy or tri-fluoromethyl, Z representsmethyl, ethyl, propyl, i-propyl, butyl, i-butyl, tert.-butyl, fluorine,chlorine, bromine, methoxy or ethoxy, n represents 0 or 1.